34160-40-2

Basic information

• Product Name: 6-Bromopyridine-2-carbaldehyde
• Synonyms: 6-BROMOPYRIDINE-2-CARBALDEHYDE;6-BROMOPYRIDINE-2-CARBOXALDEHYDE;6-BROMO-2-FORMYLPYRIDINE;6-BROMO-2-PYRIDINE CARBOXALDEHYDE;2-BROMOPYRIDINE-6-CARBOXALDEHYDE;2-BROMO-6-FORMYLPYRIDINE;6-bromopyridine-2-barboxaldehyde;6-BROMO-PYRIDINE CARBOXALDEHYDE
• CAS NO: 34160-40-2
• Molecular Formula: C₆H₄BrNO
• Molecular Weight: 186.01
• EINECS: -0
• Product Categories: Pyridine;Aldehydes;Pyridines;Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;C6Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Building Blocks;Pyridine Series;Heterocycle-Pyridine series
• Mol File: 34160-40-2.mol
• Article Data: 55

Chemical Properties

• Melting Point: 81-85 °C(lit.)
• Boiling Point: 248.2 °C at 760 mmHg
• Flash Point: 103.9 °C
• Appearance: White to beige or pale brown/Powder
• Density: 1.683 g/cm³
• Vapor Pressure: 0.0246mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: Refrigerator (+4°C)
• Solubility: Chloroform (Sparingly), Dichloromethane, Ether, Ethyl Acetate, Methanol (Slightl
• PKA: 1.00±0.10(Predicted)
• Water Solubility: Soluble in dichloromethane, ether, ethyl acetate and methanol. Insoluble in water.
• Sensitive: Air Sensitive
• BRN: 1524300
• CAS DataBase Reference: 6-Bromopyridine-2-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromopyridine-2-carbaldehyde(34160-40-2)
• EPA Substance Registry System: 6-Bromopyridine-2-carbaldehyde(34160-40-2)

Safety Data

• Hazard Codes: Xi,Xn,F
• Statements: 36/37/38-20/21/22-10
• Safety Statements: 26-36-36/37/39-16
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 34160-40-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 34160-40-2 differently. You can refer to the following data:
1. 6-Bromopyridine-2-carbaldehyde can be a useful synthetic intermediate.
2. 6-Bromopyridine-2-carboxaldehyde is used in the study of a rhodium-catalyzed, reductive aldol coupling with divinyl ketones leading to syn ?-hydroxyenones. It is also used as a building block for Tris[(pyridyl)methyl]amine ligands.

General Description

6-Bromo-2-pyridinecarboxaldehyde is a pyridine derivative. It participates in the synthesis of meso-substituted trans-A2B2-porphyrin.

InChI:InChI=1/C6H4BrNO/c7-6-3-1-2-5(4-9)8-6/h1-4H

Synthetic route

2-bromo-6-(hydroxymethyl)pyridine (33674-96-3) → 6-bromo-2-pyridinecarbaldehyde (34160-40-2)

Conditions	Yield
With fluorosulfonyl fluoride; potassium carbonate; dimethyl sulfoxide at 20℃; for 12h; chemoselective reaction;	98%
With phosphoric acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide for 1.5h; Ambient temperature;	89%
With 1-iodobenzoic acid In dimethyl sulfoxide at 20℃;
With phosphoric acid; dicyclohexyl-carbodiimide In dimethyl sulfoxide at 25℃; for 1.5h;
With 2-Iodobenzoic acid In dimethyl sulfoxide at 20℃; for 2h;

2,6-Dibromopyridine (626-05-1) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 6-bromo-2-pyridinecarbaldehyde (34160-40-2)

Conditions	Yield
Stage #1: 2,6-Dibromopyridine With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane; toluene at -10 - -5℃; for 3.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane; toluene at -10 - -5℃; for 0.5h; Further stages.;	97%
Stage #1: 2,6-Dibromopyridine With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane; toluene at -10℃; for 3h; Stage #2: N,N-dimethyl-formamide In toluene at -10 - -5℃; for 1h; Stage #3: With citric acid at 20℃; for 0.166667h;	95%
Stage #1: 2,6-Dibromopyridine With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 2h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -70 - 0℃;	94.2%

2,6-Dibromopyridine (626-05-1) + n-butyllithium (109-72-8, 29786-93-4) + butyl magnesium bromide (693-04-9) → 6-bromo-2-pyridinecarbaldehyde (34160-40-2)

Conditions	Yield
With acetic acid In tetrahydrofuran; hexane; N,N-dimethyl-formamide; toluene	95%

2-bromo-pyridine (109-04-6) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 6-bromo-2-pyridinecarbaldehyde (34160-40-2)

Conditions	Yield
Stage #1: 2-bromo-pyridine With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; for 2.5h; Inert atmosphere; Schlenk technique; Stage #2: N,N-dimethyl-formamide With zinc chloride*2(tetrahydrofuran) In tetrahydrofuran; hexane at -78 - 40℃; Inert atmosphere; Schlenk technique;	90.4%

2-bromo-6-(dibromomethyl) pyridine (82315-66-0) → 6-bromo-2-pyridinecarbaldehyde (34160-40-2)

Conditions	Yield
With calcium carbonate In water for 8h; Heating;	86%

2,6-Dibromopyridine (626-05-1) + isopropylmagnesium chloride (1068-55-9) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2,6-Pyridinedicarboxaldehyde (5431-44-7) + 6-bromo-2-pyridinecarbaldehyde (34160-40-2) + 6-isopropyl-2-pyridinecarboxaldehyde (153646-83-4)

Conditions	Yield
Stage #1: 2,6-Dibromopyridine; isopropylmagnesium chloride In tetrahydrofuran at 20℃; for 5h; Stage #2: N,N-dimethyl-formamide With acetic acid at 0℃;	A 1% B 85% C 6%

2-bromo-6-methylpyridine (5315-25-3) → 6-bromo-2-pyridinecarbaldehyde (34160-40-2)

Conditions	Yield
With selenium(IV) oxide In 1,4-dioxane at 80℃; for 16h;	71%
Multi-step reaction with 2 steps 1: 88 percent / N-bromosuccinimide; benzoylperoxide / CCl4 / 4 h / Heating 2: 86 percent / CaCO3 / H2O / 8 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 53 percent / KMnO4 / H2O / Heating 2: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min 3: 89 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme
Stage #1: 2-bromo-6-methylpyridine With bromine In dichloromethane; water at 10 - 50℃; for 10h; Stage #2: With hexamethylenetetramine In ethanol at 40℃; for 12h; Stage #3: With sulfuric acid; acetic acid In ethanol at 90℃; for 1h;	62.3 g

N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 6-bromo-2-pyridinecarbaldehyde (34160-40-2)

Conditions	Yield
Stage #1: With n-butyllithium; n-BuMgCl In tetrahydrofuran; H2O; hexane; N,N-dimethyl-formamide; toluene at -10℃; for 0.5h; Stage #2: 2,6-Dibromopyridine In tetrahydrofuran; hexane; toluene at -10℃; for 2.5h; Stage #3: N,N-dimethyl-formamide With citric acid more than 3 stages;	52%

2,6-Dibromopyridine (626-05-1) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2,6-Pyridinedicarboxaldehyde (5431-44-7) + 6-bromo-2-pyridinecarbaldehyde (34160-40-2)

Conditions	Yield
Stage #1: 2,6-Dibromopyridine With n-butyllithium; butyl magnesium bromide In tetrahydrofuran at -10℃; Stage #2: N,N-dimethyl-formamide at 0℃;	A 43% B 49%

2-(6-bromopyridinyl)lithium (37709-60-7) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 6-bromo-2-pyridinecarbaldehyde (34160-40-2)

Conditions	Yield
In tetrahydrofuran at -75℃; for 0.25h; Yield given;

2,6-Dibromopyridine (626-05-1) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2-bromo-pyridine (109-04-6) + 6-bromo-2-pyridinecarbaldehyde (34160-40-2) + 2,6-dibromo-pyridine-3-carbaldehyde (55304-83-1)

Conditions	Yield
Stage #1: 2,6-Dibromopyridine With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran Further stages.;

2-Amino-6-methylpyridine (1824-81-3) → 6-bromo-2-pyridinecarbaldehyde (34160-40-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: HBr; Br2 / H2O / 0.83 h / -20 °C 1.2: NaNO2 / H2O / 2.5 h / -20 °C 2.1: 88 percent / N-bromosuccinimide; benzoylperoxide / CCl4 / 4 h / Heating 3.1: 86 percent / CaCO3 / H2O / 8 h / Heating View Scheme
Multi-step reaction with 4 steps 1: 82 percent / NaNO2, Br2, 48percent HBr / 5 °C 2: 53 percent / KMnO4 / H2O / Heating 3: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min 4: 89 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme

2,6-Dibromopyridine (626-05-1) → 6-bromo-2-pyridinecarbaldehyde (34160-40-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-BuLi / tetrahydrofuran / -78 °C 1.2: tetrahydrofuran / -78 °C 1.3: NaBH4 / tetrahydrofuran / 0 °C 2.1: 1-iodobenzoic acid / dimethylsulfoxide / 20 °C View Scheme
Multi-step reaction with 3 steps 1: n-BuLi / tetrahydrofuran / -78 °C / addition of 2,6-dibromopyridine to a solution of BuLi 2: n-BuLi / tetrahydrofuran / 0.25 h / -78 °C / addition of 2,6-dibromopyridine into a solution of dilithiopyridine 3: tetrahydrofuran / 0.25 h / -75 °C View Scheme
With hydrogenchloride; n-butyllithium In N-methyl-acetamide; hexane
With hydrogenchloride
With n-butyllithium; acetic acid In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide	3.33 g (18.0 mmol, 84%)

2,6-dilithiopyridine → 6-bromo-2-pyridinecarbaldehyde (34160-40-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: n-BuLi / tetrahydrofuran / 0.25 h / -78 °C / addition of 2,6-dibromopyridine into a solution of dilithiopyridine 2: tetrahydrofuran / 0.25 h / -75 °C View Scheme

6-bromo-pyridine-2-carboxylic acid (21190-87-4) → 6-bromo-2-pyridinecarbaldehyde (34160-40-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min 2: 89 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme

2,6-Dibromopyridine (626-05-1) + NBuli → 6-bromo-2-pyridinecarbaldehyde (34160-40-2)

Conditions	Yield
With hydrogenchloride In N,N-dimethyl-formamide

2,6-Dibromopyridine (626-05-1) + di-isopropyl ether (108-20-3) → 6-bromo-2-pyridinecarbaldehyde (34160-40-2)

Conditions	Yield
With n-butyllithium; ammonium chloride In tetrahydrofuran; N,N-dimethyl-formamide

6-bromo-2-(2,6-diisopropylphenyl)iminopyridine (1127647-91-9) + 1-Naphthylboronic acid (13922-41-3) → 6-bromo-2-pyridinecarbaldehyde (34160-40-2) + 6-(1-naphthyl)-2-[(2,6-diisopropylphenyl)imino]pyridine (1169702-61-7)

Conditions	Yield
tetrakis(triphenylphosphine)palladium (0) In ethanol; water; toluene

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + 4-methoxy-aniline (104-94-9) → C13H11BrN2O

Conditions	Yield
for 6h; Molecular sieve; Reflux;	100%
In acetonitrile at 20℃; for 0.166667h;
In [D3]acetonitrile at 25℃; for 0.0833333h; Kinetics; Time;

6-bromo-2-pyridinecarbaldehyde (34160-40-2) → 6-bromopyridine-2-carbaldehyde oxime

Conditions	Yield
With sodium acetate; hydroxylamine sulfate In ethanol at 20℃; for 16h; Inert atmosphere;	100%
With hydroxylamine hydrochloride; sodium acetate In ethanol at 90℃;	99%
With hydroxylamine hydrochloride; sodium acetate In ethanol at 20℃; for 16h;	90%
With hydroxylamine hydrochloride; sodium acetate In ethanol at 20℃;

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + dibenzo[b,d]thiophen-3-ylboronic acid → 6-(dibenzo[b,d]thiophen-3-yl)picolinaldehyde

Conditions	Yield
With potassium phosphate monohydrate; C66H84O10P2Pd In water; ethyl acetate; toluene at 45℃; for 14h; Suzuki-Miyaura Coupling; Inert atmosphere;	100%

N-methyl-N-(pyridin-2-yl)hydrazine (4231-74-7) + 6-bromo-2-pyridinecarbaldehyde (34160-40-2) → C12H11BrN4

Conditions	Yield
for 6h; Molecular sieve; Reflux;	100%
In [D3]acetonitrile at 25℃; for 0.0833333h; Time;

3,5-di-tert-butyl-2-methoxyphenyl boronic acid (245434-15-5) + 6-bromo-2-pyridinecarbaldehyde (34160-40-2) → 6-(3,5-di-tert-butyl-2-methoxyphenyl)picolinaldehyde

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 90℃; for 20h; Suzuki Coupling;	100%

6-bromo-2-pyridinecarbaldehyde (34160-40-2) → 2-bromo-6-(hydroxymethyl)pyridine (33674-96-3)

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 1h;	99%
With sodium tetrahydroborate In ethanol	99%
With methanol; sodium tetrahydroborate In methanol at 0 - 20℃; for 0.5h;	99%

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + trimethyl orthoformate (149-73-5) → 2-bromo-6-(dimethoxymethyl)pyridin (128507-76-6)

Conditions	Yield
With toluene-4-sulfonic acid In methanol for 4h; Reflux; Inert atmosphere; Schlenk technique;	99%
With toluene-4-sulfonic acid In methanol for 4h; Reflux;	98%
toluene-4-sulfonic acid In methanol for 1h; Heating;	96%

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + phenylboronic acid (98-80-6) → 6-phenylpyridine-2-carbaldehyde (157402-44-3)

Conditions	Yield
With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In tetrahydrofuran for 18h; Inert atmosphere; Reflux;	99%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 120℃; for 6h; Inert atmosphere;	98%
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane; water at 100℃; for 16h;	94.6%

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + 4-(N,N-dimethylaminocarbonyl)phenylboronic acid (405520-68-5) → 4-(6-formylpyridin-2-yl)-N,N-dimethylbenzamide (1610373-10-8)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 90℃; for 3h; Inert atmosphere;	99%

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + diethylamine (109-89-7) → (6-bromopyridin-2-ylmethyl)diethylamine (174608-36-7)

Conditions	Yield
Stage #1: 6-bromo-2-pyridinecarbaldehyde; diethylamine In 1,2-dichloro-ethane at 20℃; for 0.0166667h; Inert atmosphere; Schlenk technique; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 1.5h; Inert atmosphere; Schlenk technique;	99%
With sodium tris(acetoxy)borohydride In dichloromethane at 0 - 20℃; for 2h;	2.31 g

propylamine (107-10-8) + 6-bromo-2-pyridinecarbaldehyde (34160-40-2) → N-[(6-bromopyridin-2-yl)methyl]propan-1-amine (1366406-65-6)

Conditions	Yield
With sodium tris(acetoxy)borohydride In chloroform at 20℃; for 0.75h;	99%

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + phosphorohydrazidic acid diethyl ester (56183-69-8) → diethyl N'-(6-bromopyridin-2-yl)methylenephosphorohydrazidate

Conditions	Yield
In dichloromethane for 1.5h; Reflux; Dean-Stark; Inert atmosphere;	99%

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + diethyl 1-cyanomethylphosphonate (2537-48-6) → C8H5BrN2

Conditions	Yield
Stage #1: diethyl 1-cyanomethylphosphonate With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 6-bromo-2-pyridinecarbaldehyde In tetrahydrofuran at 0℃; for 0.5h;	99%

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + 2,6-dimethylaniline (87-62-7) → C14H13BrN2

Conditions	Yield
In ethanol for 4h; Inert atmosphere; Reflux;	99%

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + 2,6-diisopropylbenzenamine (24544-04-5) → (6-bromo-pyridin-2-yl-methylene)-(2,6-diisopropyl-phenyl)-amine (706819-98-9)

Conditions	Yield
With formic acid In ethanol for 2 - 3h; Inert atmosphere; Schlenk technique; Reflux;	98%
With magnesium sulfate In diethyl ether at 20℃; Inert atmosphere; Schlenk technique;	98%
With toluene-4-sulfonic acid In toluene at 70℃; for 12h; Molecular sieve;	90.5%

methanol (67-56-1) + 6-bromo-2-pyridinecarbaldehyde (34160-40-2) → methyl 6-Bromopicolinate (26218-75-7)

Conditions	Yield
With water; iodine; sodium nitrite at 20 - 70℃; chemoselective reaction;	98%

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + acetic acid (64-19-7) → (E)-3-(6-bromopyridin-2-yl)acrylic acid

Conditions	Yield
Stage #1: 6-bromo-2-pyridinecarbaldehyde; acetic acid With titanium tetrachloride In dichloromethane at 25℃; for 0.333333h; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at 25℃; Inert atmosphere; stereoselective reaction;	98%

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + 2-amino-benzenethiol (137-07-5) → 2-(6-bromopyridin-2-yl)benzo[d]thiazole

Conditions	Yield
In ethanol at 20℃;	98%
With amberlite IR-120(H)resin In water at 85℃; Sonication; Microwave irradiation;	96%
In water at 60℃; for 1h; Sonication;	90%

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + (Z)-3-bromocyclooct-1-ene (7422-06-2) → (6-bromopyridin-2-yl)((Z)-cyclooct-2-en-1-yl)methanol

Conditions	Yield
With bismuth; lithium iodide In N,N-dimethyl-formamide at 20℃; for 12h; diastereoselective reaction;	98%

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + 2,6-dimethylbenzene boronic acid (100379-00-8) → 6-(2,6-dimethylphenyl)picolinaldehyde

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 90℃; for 16h; Inert atmosphere;	97%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol; toluene at 80℃;

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + 2,6-diisopropylbenzenamine (24544-04-5) → N-[(1E)-(6-bromopyridin-2-yl)methylene]-2,6-diisopropylaniline

Conditions	Yield
In ethanol for 2h; Heating;	97%
In ethanol for 8h; Reflux;
With toluene-4-sulfonic acid In toluene for 0.25h; Reflux;	23.9 g

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + acrylic acid methyl ester (292638-85-8) → methyl 2-[(6-bromopyridin-2-yl)(hydroxy)methyl]prop-2-enoate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane at 20℃; for 7h; Sonication;	97%
With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; water at 20℃; for 3h; Morita-Baylis-Hillman Alkylation;

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + orthoformic acid triethyl ester (122-51-0) → 2-bromo-6-(diethoxymethyl)pyridine (147133-45-7)

Conditions	Yield
With toluene-4-sulfonic acid In ethanethiol at 20℃; for 3h; Inert atmosphere; Schlenk technique;	97%
With toluene-4-sulfonic acid In ethanol at 20℃; for 3h; Inert atmosphere; Schlenk technique;	96%
With toluene-4-sulfonic acid In ethanol Inert atmosphere; Reflux;	76.5%

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + 4-Chlorophenylboronic acid (1679-18-1) → 6-(4-chlorophenyl)-2-pyridinecarboxaldehyde (61704-30-1)

Conditions	Yield
With C64H118O20; C54H72NO6PPdS; triethylamine In water at 45℃; for 16h; Reagent/catalyst; Suzuki-Miyaura Coupling; Inert atmosphere;	97%
With C35H47O3P*C15H16N(1-)*CH3O3S(1-)*Pd(2+); triethylamine In water at 45℃; for 15h; Suzuki-Miyaura Coupling;	94%
With TPGS-750-M; palladacycle A; triethylamine In tetrahydrofuran; water at 45℃; for 16h; Inert atmosphere;

2-amino-5-ethyl-1,3,4-thiadiazole (14068-53-2) + 6-bromo-2-pyridinecarbaldehyde (34160-40-2) + phosphonic acid diethyl ester (762-04-9) → diethyl ((6-bromopyridin-2-yl)((5-5-ethyl-1,3,4-thiadiazol-2-yl)amino)methyl)phosphonate

Conditions	Yield
With phospho sulphonic acid In neat (no solvent) for 0.108333h; Kabachnik-Fields Reaction; Microwave irradiation; Green chemistry;	96.5%

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + ethylene glycol (107-21-1) → 2-bromo-6-(1,3-dioxolan-2-yl)pyridine (34199-87-6)

Conditions	Yield
With toluene-4-sulfonic acid In benzene at 100℃; for 24h; Inert atmosphere; Dean-Stark;	96%
With toluene-4-sulfonic acid In benzene at 100℃; for 24h; Dean-Stark; Inert atmosphere;	96%
With toluene-4-sulfonic acid In toluene at 130℃; for 48h; Inert atmosphere; Dean-Stark;	95%

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + 2-methoxyethylamine (109-85-3) → N-[(6-bromopyridin-2-yl)methyl]-2-methoxyethaneamine (866327-71-1)

Conditions	Yield
Stage #1: 6-bromo-2-pyridinecarbaldehyde; 2-methoxyethylamine In dichloromethane at 20℃; for 0.166667h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; Stage #3: With hydrogenchloride; water In dichloromethane pH=4;	96%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 6-bromo-2-pyridinecarbaldehyde (34160-40-2) → C10H10BrNO2 (229008-97-3)

Conditions	Yield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: 6-bromo-2-pyridinecarbaldehyde In tetrahydrofuran at 0 - 20℃; Horner-Wadsworth-Emmons reaction; Inert atmosphere;	96%
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 15h; Horner-Wadsworth-Emmons Olefination;	56%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.25h; Stage #2: 6-bromo-2-pyridinecarbaldehyde In tetrahydrofuran; mineral oil at 0 - 20℃;	56%

Upstream product

• 626-05-1 2,6-Dibromopyridine 
• 1068-55-9 isopropylmagnesium chloride 
• 68-12-2 N,N-dimethyl-formamide 
• 109-72-8 n-butyllithium 
• 693-04-9 butyl magnesium bromide 
• 109-04-6 2-bromo-pyridine 
• 1127647-91-9 6-bromo-2-(2,6-diisopropylphenyl)iminopyridine 
• 13922-41-3 1-Naphthylboronic acid 
• 108-20-3 di-isopropyl ether 
• 21190-87-4 6-bromo-pyridine-2-carboxylic acid 
• 5315-25-3 2-bromo-6-methylpyridine 
• 1824-81-3 2-Amino-6-methylpyridine 
• 82315-66-0 2-bromo-6-(dibromomethyl) pyridine 
• 37709-60-7 2-(6-bromopyridinyl)lithium 

Downstream Products

• 139163-56-7 (+/-)-1-[2-(6-bromopyridyl)]ethanol 
• 33674-96-3 2-bromo-6-(hydroxymethyl)pyridine 
• 157402-44-3 6-phenylpyridine-2-carbaldehyde 
• 61704-38-9 6-(3-chloro-phenyl)-pyridine-2-carbaldehyde 
• 502925-47-5 6-(4-methoxyphenyl)pyridin-2-ylcarboxyaldehyde 
• 52583-70-7 6-(3-nitrophenyl)-2-pyridinecarboxaldehyde 
• 866613-65-2 6-(2-methoxyphenyl)-2-pyridinecarboxaldehyde 
• 502925-44-2 6-[3-(trifluoromethyl)phenyl]-2-pyridinecarbaldehyde 
• 502925-49-7 6-o-d1-phenyl-2-pyridinecarboxaldehyde 
• 912295-39-7 6-mesityl-pyridine-2-carboxaldehyde 
• 638214-10-5 6-[4-(trifluoromethyl)phenyl]-2-pyridinecarbaidehyde 
• 746668-89-3 [(6-bromo-pyridin-2-yl)-phenylamino-methyl]-phosphonic acid diphenyl ester 
• 857283-88-6 6-morpholin-4-ylpyridine-2-carbaldehyde 
• 909714-12-1 6-carbazolylpyridine-2-carboxaldehyde 

Relevant articles and documents

Non-symmetrical, potentially redox non-innocent imino NHC pyridine 'pincers': Via a zinc ion template-assisted synthesis

New non-symmetrical, redox-active imino NHC pyridine pincer ligands, 2-(R1-imidazol-2-ylidene)-6-(R2NCH)-pyridine (R1 = 2,6-diisopropylphenyl (DiPP), R2 = 2,4,6-trimethylphenyl (Mes), 4B; R1 = R2 = DiPP, 4C), have been accessed by a ZnII-promoted modular synthesis involving the quaternization of R1-imidazole by [Zn(κNimineκNpyridine)(2-(R2NCH)-6-bromo-pyridine)Cl2], followed by ZnII removal and deprotonation of imidazolium pro-ligands. Redox active forms of 4B were implicated in the two complexes obtained by its reaction with FeBr2/KC8; metrical data analysis pointed to the occurrence of radical anionic and dianionic redox states of 4B.

Synthesis, Structures, and Norbornene Polymerization Behavior of Imidazo[1,5- a]pyridine-sulfonate-Ligated Palladacycles

Two imidazo[1,5-a]pyridine-sulfonate proligands, L1 and L2, were synthesized in five-step reactions. Treatment of the proligands with palladacycles {[Pd(OAc)(8-Me-quin-H)]2, [Pd(dmba)(μ-Cl)]2, and [Pd(o-acetanilido)(μ-trifluoroacetato)]2} yielded the desired five-membered C(sp3),N-chelated (Pd1, Pd2), C(sp2),N-chelated (Pd3, Pd4), and six-membered C(sp2),O-chelated (Pd5, Pd6) palladacycles, respectively. All these complexes were fully characterized by 1H and 13C NMR, IR, high-resolution mass spectrometry, and elemental analysis. The molecular structures of complexes Pd1, Pd2, Pd4, and Pd5 were determined by single-crystal X-ray diffraction analysis. In the presence of MAO or Et2AlCl, Pd1-Pd6 exhibited activities toward the addition polymerization of norbornene which decreased in the order Pd6 > Pd5 > Pd4 > Pd2 > Pd3 > Pd1. The Pd1-Pd6/MAO catalytic system showed high thermal stability and reached the highest activity at 100 °C (6.0 × 107 g of PNB (mol of Pd)-1 h-1 with 99.9% conversion). In the presence of Et2AlCl with low loading (100 equiv), Pd5 and Pd6 exhibited high activities (up to 2.9 × 107 g of PNB (mol of Pd)-1 h-1 with 96.5% conversion). It was demonstrated that the structures of palladacycles and the substituents on the ligands significantly affected the activities of these complexes.

Adenosine receptor antagonists

The invention provides a compound shown as a formula (I) and a pharmaceutical composition thereof. The compounds of formula (I) of the present invention are useful as adenosine receptor inhibitors, especially A2A and/or A2B inhibitors, for example, the product can be used for prevention or treatment of diseases associated with A2A and/or A2B activity or expression.

Highly efficient palladium-catalysed carbon dioxide hydrosilylation employing PMP ligands

A series of zero-valent palladium complexes featuring diphosphinometal ligands is reported. The metalloligand in the PMP-type framework (M = LiI, CuI, ZnII) acts as a weak to medium acceptor ligand for palladium. A Pd0→ZnII bond was observed in the solid state and further confirmed by NBO analysis. The heterobimetallic Pd/Zn complex 2-Zn displayed excellent activity in chemoselective CO2 hydrosilylation producing silyl formate (TOF1/2 = 3000 h?1).