120578-03-2

Basic information

• Product Name: 3-(2-(7-CHLOROQUINOLINE-2-YL)-(E)-VINYL)BENZALDEHYDE
• Synonyms: 3-(2-(7-CHLOROQUINOLINE-2-YL)-(E)-VINYL)BENZALDEHYDE;(E)-3-2-7-Chloro-2-Quinolinyl)-Vinyl-Benzaldehyde;3-[(E)-2-(7-CHLORO-2-QUINOLYL)VINYL]BENZALDEHYDE;(E)-3-[2-(7-Chloro-2-quinolinyl)ethenyl]benzaldehyde;Benzaldehyde,3-[(1E)-2-(7-chloro-2-quinolinyl)ethenyl]-;3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]benzaldehyde;(E)-3-(2-(7-chloroquinolin-2-yl)vinyl)benzaldehyde;3-(2-(7-Chloroquinolin-2-yl)vinyl)benzaldehyde
• CAS NO: 120578-03-2
• Molecular Formula: C₁₈H₁₂ClNO
• Molecular Weight: 293.75
• EINECS: 421-800-1
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 120578-03-2.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 476.502 °C at 760 mmHg
• Flash Point: 241.98 °C
• Appearance: Pale yellow solid
• Density: 1.314 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.751
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 2.09±0.61(Predicted)
• CAS DataBase Reference: 3-(2-(7-CHLOROQUINOLINE-2-YL)-(E)-VINYL)BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-(7-CHLOROQUINOLINE-2-YL)-(E)-VINYL)BENZALDEHYDE(120578-03-2)
• EPA Substance Registry System: 3-(2-(7-CHLOROQUINOLINE-2-YL)-(E)-VINYL)BENZALDEHYDE(120578-03-2)

Safety Data

• Hazardous Substances Data: 120578-03-2(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Uses

Intermediate in the production of Leukotriene receptor antagonists.

InChI:InChI=1/C18H12ClNO/c19-16-7-5-15-6-9-17(20-18(15)11-16)8-4-13-2-1-3-14(10-13)12-21/h1-12H/b8-4+

Synthetic route

2-methyl-7-chloroquinoline (4965-33-7) + Isophthalaldehyde (626-19-7) → (E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2)

Conditions	Yield
With lanthanum pentafluorobenzoate In toluene at 120℃; for 24h;	97%
With tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate In neat (no solvent) at 130℃; Green chemistry;	93%
With acetic anhydride In toluene at 100 - 105℃; for 12 - 15h;	75.15%

2-methyl-7-chloroquinoline (4965-33-7) + Isophthalaldehyde (626-19-7) → (E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) + C28H18Cl2N2 (120578-04-3)

Conditions	Yield
With acetic acid at 100℃; Product distribution / selectivity;	A 65.45% B 7.75%
With acetic anhydride In xylene for 7h; Heating; Yield given;
With acetic anhydride In xylene for 7h; Heating; Yields of byproduct given;

2-((S)-3-Acetoxy-1-bromo-3-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-propyl)-benzoic acid methyl ester (184763-69-7) → (E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) + trans-3-[2-(7-chloroquinolin-2-yl)ethenyl]benzyl alcohol (139425-04-0) + 3-[(E)-2-(7-chloro-2-quinolyl)vinyl]benzoic acid (203940-18-5) + 2-((S)-1-Bromo-3-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-3-hydroxy-propyl)-benzoic acid (1026009-57-3)

Conditions	Yield
With lithium hydroxide In tetrahydrofuran; methanol at 23℃; for 24h;

methyl-[(E)]-2-[3(S)-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl] benzoate (181139-72-0) → (E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 99 percent / Et3N, 4-DMAP / CH2Cl2 / 0.25 h 2: 69 percent / NBS, (BzO)2 / CCl4 / 3 h / Heating 3: 1 N LiOH / tetrahydrofuran; methanol / 24 h / 23 °C View Scheme

2-((S)-3-Acetoxy-3-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-propyl)-benzoic acid methyl ester (184763-59-5) → (E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / NBS, (BzO)2 / CCl4 / 3 h / Heating 2: 1 N LiOH / tetrahydrofuran; methanol / 24 h / 23 °C View Scheme

2-methyl-7-chloroquinoline (4965-33-7) → (E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2)

Conditions	Yield
In Isophthalaldehyde

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) + ethylene glycol (107-21-1) → 2-<3-<2-(7-chloro-2-quinolinyl)-(E)-ethenyl>phenyl>-1,3-dioxolane (143816-71-1)

Conditions	Yield
In toluene Heating;	98%

vinyl magnesium bromide (1826-67-1) + (E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) → trans-3-[2-(7-chloroquinolin-2-yl)ethenyl]benzyl alcohol (139425-04-0) + (E)-3-<2-(7-chloro-2-quinolinyl)ethenyl>-α-ethenylphenylmethanol (149968-10-5)

Conditions	Yield
In tetrahydrofuran; toluene at 0 - 5℃; for 1h; Yields of byproduct given;	A n/a B 92%

vinylmagnesium chloride (3536-96-7) + (E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) → (E)-3-<2-(7-chloro-2-quinolinyl)ethenyl>-α-ethenylphenylmethanol (149968-10-5)

Conditions	Yield
In tetrahydrofuran; ethylbenzene at -15℃;	91%
Stage #1: vinylmagnesium chloride; (E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde In tetrahydrofuran; toluene at 0 - 10℃; for 1.5h; Stage #2: With ammonium acetate; water In tetrahydrofuran; toluene for 1h;

methylmagnesium chloride (676-58-4) + (E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) → 3-(7-Chloroquinol-2-yl-trans-ethenyl)-alpha-methylbenzyl alcohol (139425-24-4)

Conditions	Yield
Stage #1: methylmagnesium chloride; (E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde In tetrahydrofuran at -10 - 5℃; for 2.75h; Stage #2: With water at 10 - 15℃; for 0.5h;	89.43%
In tetrahydrofuran; toluene at -10℃; for 2h; Inert atmosphere;	78%
In tetrahydrofuran; toluene at -10℃; for 2h; Inert atmosphere;	78%
Stage #1: methylmagnesium chloride; (E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde In toluene at -5℃; for 2h; Stage #2: With water; ammonium chloride In toluene at 5℃; for 2h; Product distribution / selectivity;

Methyl 3-mercaptopropionate (2935-90-2) + (E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) → dimethyl 5-<3-<2-(7-chloro-2-quinolinyl)-(E)-ethenyl>phenyl>-4,6-dithianonanedioate (120385-96-8)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at -5 - 0℃; for 2h;	87%

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) + acetone (67-64-1) → (E)-4-{3-[(E)-2-(7-chloroquinolin-2-yl)vinyl]phenyl}but-3-en-2-one (1429879-31-1)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water for 3h;	76.47%
With sodium hydroxide In tetrahydrofuran; water for 3h;	76.47%

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) + dimethyl sulfoxide (67-68-5) → 7-chloro-2-[(E)-2-(3-oxiranylphenyl)vinyl]quinoline (1429879-00-4)

Conditions	Yield
With trimethylsulphonium iodide; sodium hydride In tetrahydrofuran; dimethyl sulfoxide for 2h; Inert atmosphere;	66%
With trimethylsulphonium iodide; sodium hydride In tetrahydrofuran for 2h; Inert atmosphere;	66%

Methyl 3-mercaptopropionate (2935-90-2) + (E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) + N,N-dimethyl-3-mercaptopropionamide (92065-71-9) → (+)-methyl 5-(3-(2-(7-chloroquinoline-2-yl)ethenyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate (120443-15-4)

Conditions	Yield
With boron trifluoride diethyl etherate In chloroform at -8 - 2℃; for 2h;	49%

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) + ethyl bromoacetate (105-36-2) → ethyl 3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-hydroxypropanoate (1095202-12-2)

Conditions	Yield
Stage #1: (E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde With zinc In diethyl ether; toluene at 60 - 70℃; for 0.5 - 0.75h; Stage #2: ethyl bromoacetate In diethyl ether; toluene at 60 - 70℃; for 3h;	46%

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) → trans-3-[2-(7-chloroquinolin-2-yl)ethenyl]benzyl alcohol (139425-04-0) + (E)-3-<2-(7-chloro-2-quinolinyl)ethenyl>-α-ethenylphenylmethanol (149968-10-5)

Conditions	Yield
With vinyl magnesium bromide In tetrahydrofuran at 0 - 5℃; for 1h;	A 40% B n/a

Methyl 3-mercaptopropionate (2935-90-2) + (R)-(-)-α-methoxyphenylthiolacetic acid (115104-46-6) + (E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) → 3-[(R)-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-((R)-2-methoxy-2-phenyl-acetylsulfanyl)-methylsulfanyl]-propionic acid methyl ester (130066-18-1) + 3-[(S)-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-((R)-2-methoxy-2-phenyl-acetylsulfanyl)-methylsulfanyl]-propionic acid methyl ester (130066-19-2)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; boron trifluoride diethyl etherate In 1,2-dichloro-ethane for 24h; Ambient temperature; Yield given. Yields of byproduct given;

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) + N,N-dimethyl-3-mercaptopropionamide (92065-71-9) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 3-({3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-trimethylsilanyloxy-methylsulfanyl)-N,N-dimethyl-propionamide (120578-06-5)

Conditions	Yield
With 1H-imidazole In dichloromethane at 12 - 14℃; for 24h;

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) → -1-<2-<3-<3-<2-(7-chloro-2-quinolinyl)ethenyl>phenyl>-3-hydroxypropyl>phenyl>ethanone (150026-73-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / toluene; tetrahydrofuran / 1 h / 0 - 5 °C 2: 83 percent / Et3N / Pd(OAc)2 / acetonitrile / 12 h / Heating 3: 87.1 percent / (-)-α-pinene, chloroborane-methyl sulfide, diisopropylethylamine / hexane; tetrahydrofuran / 1) -20 deg C, 3.5 h, 2) to 0 deg C, 1 h 4: 1) lithium hexamethyldisilazide / 1) THF, 2) toluene, 0 deg C, 1 h View Scheme
Multi-step reaction with 4 steps 1: vinylmagnesium bromide / tetrahydrofuran / 1 h / 0 - 5 °C 2: 83 percent / Et3N / Pd(OAc)2 / acetonitrile / 12 h / Heating 3: 87.1 percent / (-)-α-pinene, chloroborane-methyl sulfide, diisopropylethylamine / hexane; tetrahydrofuran / 1) -20 deg C, 3.5 h, 2) to 0 deg C, 1 h 4: 1) lithium hexamethyldisilazide / 1) THF, 2) toluene, 0 deg C, 1 h View Scheme

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) → methyl 2-(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-oxopropyl)benzoate (149968-11-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / toluene; tetrahydrofuran / 1 h / 0 - 5 °C 2: 83 percent / Et3N / Pd(OAc)2 / acetonitrile / 12 h / Heating View Scheme
Multi-step reaction with 2 steps 1: vinylmagnesium bromide / tetrahydrofuran / 1 h / 0 - 5 °C 2: 83 percent / Et3N / Pd(OAc)2 / acetonitrile / 12 h / Heating View Scheme

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) → Methanesulfonic acid (R)-3-(2-acetyl-phenyl)-1-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-propyl ester

Conditions	Yield
Multi-step reaction with 5 steps 1: 92 percent / toluene; tetrahydrofuran / 1 h / 0 - 5 °C 2: 83 percent / Et3N / Pd(OAc)2 / acetonitrile / 12 h / Heating 3: 87.1 percent / (-)-α-pinene, chloroborane-methyl sulfide, diisopropylethylamine / hexane; tetrahydrofuran / 1) -20 deg C, 3.5 h, 2) to 0 deg C, 1 h 4: 1) lithium hexamethyldisilazide / 1) THF, 2) toluene, 0 deg C, 1 h 5: Et3N / toluene / 1 h / -5 °C View Scheme
Multi-step reaction with 5 steps 1: vinylmagnesium bromide / tetrahydrofuran / 1 h / 0 - 5 °C 2: 83 percent / Et3N / Pd(OAc)2 / acetonitrile / 12 h / Heating 3: 87.1 percent / (-)-α-pinene, chloroborane-methyl sulfide, diisopropylethylamine / hexane; tetrahydrofuran / 1) -20 deg C, 3.5 h, 2) to 0 deg C, 1 h 4: 1) lithium hexamethyldisilazide / 1) THF, 2) toluene, 0 deg C, 1 h 5: Et3N / toluene / 1 h / -5 °C View Scheme

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) → L 699392

Conditions	Yield
Multi-step reaction with 6 steps 1: 92 percent / toluene; tetrahydrofuran / 1 h / 0 - 5 °C 2: 83 percent / Et3N / Pd(OAc)2 / acetonitrile / 12 h / Heating 3: 87.1 percent / (-)-α-pinene, chloroborane-methyl sulfide, diisopropylethylamine / hexane; tetrahydrofuran / 1) -20 deg C, 3.5 h, 2) to 0 deg C, 1 h 4: 1) lithium hexamethyldisilazide / 1) THF, 2) toluene, 0 deg C, 1 h 5: Et3N / toluene / 1 h / -5 °C 6: 1) BuLi / 1) THF, hexane, -75 to 10 deg C, 1 h, 2) toluene, 20 deg C, 2 h View Scheme
Multi-step reaction with 6 steps 1: vinylmagnesium bromide / tetrahydrofuran / 1 h / 0 - 5 °C 2: 83 percent / Et3N / Pd(OAc)2 / acetonitrile / 12 h / Heating 3: 87.1 percent / (-)-α-pinene, chloroborane-methyl sulfide, diisopropylethylamine / hexane; tetrahydrofuran / 1) -20 deg C, 3.5 h, 2) to 0 deg C, 1 h 4: 1) lithium hexamethyldisilazide / 1) THF, 2) toluene, 0 deg C, 1 h 5: Et3N / toluene / 1 h / -5 °C 6: 1) BuLi / 1) THF, hexane, -75 to 10 deg C, 1 h, 2) toluene, 20 deg C, 2 h View Scheme

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) → -2-<3-<3-<2-(7-chloro-2-quinolinyl)ethenyl>phenyl>-3-hydroxypropyl>benzoic acid methyl ester (150026-72-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / toluene; tetrahydrofuran / 1 h / 0 - 5 °C 2: 83 percent / Et3N / Pd(OAc)2 / acetonitrile / 12 h / Heating 3: 87.1 percent / (-)-α-pinene, chloroborane-methyl sulfide, diisopropylethylamine / hexane; tetrahydrofuran / 1) -20 deg C, 3.5 h, 2) to 0 deg C, 1 h View Scheme
Multi-step reaction with 3 steps 1: vinylmagnesium bromide / tetrahydrofuran / 1 h / 0 - 5 °C 2: 83 percent / Et3N / Pd(OAc)2 / acetonitrile / 12 h / Heating 3: 87.1 percent / (-)-α-pinene, chloroborane-methyl sulfide, diisopropylethylamine / hexane; tetrahydrofuran / 1) -20 deg C, 3.5 h, 2) to 0 deg C, 1 h View Scheme

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) → methyl-[(E)]-2-[3(S)-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl] benzoate (181139-72-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / toluene; tetrahydrofuran / 1 h / 0 - 5 °C 2: 83 percent / Et3N / Pd(OAc)2 / acetonitrile / 12 h / Heating 3: 87.1 percent / (+)-α-pinene, chloroborane-methyl sulfide, diisopropylethylamine / hexane; tetrahydrofuran / 1) -20 deg C, 3.5 h, 2) to 0 deg C, 1 h View Scheme
Multi-step reaction with 3 steps 1: vinylmagnesium bromide / tetrahydrofuran / 1 h / 0 - 5 °C 2: 83 percent / Et3N / Pd(OAc)2 / acetonitrile / 12 h / Heating 3: 87.1 percent / (+)-α-pinene, chloroborane-methyl sulfide, diisopropylethylamine / hexane; tetrahydrofuran / 1) -20 deg C, 3.5 h, 2) to 0 deg C, 1 h View Scheme

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) → trans-3-<2-(7-chloro-2-quinolinyl)cyclopropyl>benzaldehyde (115104-43-3, 143816-73-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 98 percent / toluene / Heating 2: 1.) n-BuLi / 1.) THF, from -10 deg C to 21 deg C, 2 h, 2.) THF, 0 deg C, overnight 3: 97 percent / tetrahydrofuran; acetic acid; H2O / 2 h / Heating View Scheme

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) → trans-2-<3-<2-(7-chloro-2-quinolinyl)cyclopropyl>phenyl>-1,3-dioxolane (115104-42-2, 143816-72-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 98 percent / toluene / Heating 2: 1.) n-BuLi / 1.) THF, from -10 deg C to 21 deg C, 2 h, 2.) THF, 0 deg C, overnight View Scheme

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) → trans-5-<3-<2-(7-chloro-2-quinolinyl)cyclopropyl>phenyl>-4,6-dithianonanedioic acid (115104-03-5, 143816-58-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 98 percent / toluene / Heating 2: 1.) n-BuLi / 1.) THF, from -10 deg C to 21 deg C, 2 h, 2.) THF, 0 deg C, overnight 3: 97 percent / tetrahydrofuran; acetic acid; H2O / 2 h / Heating 4: 71 percent / p-TsOH / toluene / 4.5 h / Heating View Scheme

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) → (E)-5-(3-(2-(7-chloroquinolin-2-yl)ethenyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoic acid (135028-15-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 49 percent / BF3*Et2O / CHCl3 / 2 h / -8 - 2 °C 2: 88 percent / 1.00 N aq. LiOH / tetrahydrofuran / 4.5 h / -3 - 2 °C View Scheme
Multi-step reaction with 3 steps 1: imidazole / CH2Cl2 / 24 h / 12 - 14 °C 2: 61 percent / BF3*Et2O / CH2Cl2 / 16 h / -50 °C 3: 88 percent / 1.00 N aq. LiOH / tetrahydrofuran / 4.5 h / -3 - 2 °C View Scheme

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) → (+)-methyl 5-(3-(2-(7-chloroquinoline-2-yl)ethenyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate (120443-15-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: imidazole / CH2Cl2 / 24 h / 12 - 14 °C 2: 61 percent / BF3*Et2O / CH2Cl2 / 16 h / -50 °C View Scheme

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) → 3-[{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-(2-dimethylcarbamoyl-ethylsulfanyl)-methylsulfanyl]-N,N-dimethyl-propionamide (120578-05-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: imidazole / CH2Cl2 / 24 h / 12 - 14 °C 2: BF3*Et2O / CH2Cl2 / 16 h / -50 °C View Scheme

(2S,3S)-3-mercapto-2-methylbutanoic acid (863708-50-3) + (E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (120578-03-2) → (2S,3S,2'S,3'S)-3,3'-[({3-[(E)-2-(7-chloroquinolin-2-yl)vinyl]phenyl}methylene)bis(thio)]bis(2-methylbutanoic acid) (863708-45-6)

Conditions	Yield
With trifluoroacetic acid at 20℃; for 0.25h;

Upstream product

• 4965-33-7 2-methyl-7-chloroquinoline 
• 626-19-7 Isophthalaldehyde 
• 184763-59-5 2-((S)-3-Acetoxy-3-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-propyl)-benzoic acid methyl ester 
• 181139-72-0 methyl-[(E)]-2-[3(S)-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl] benzoate 
• 184763-69-7 2-((S)-3-Acetoxy-1-bromo-3-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-propyl)-benzoic acid methyl ester 

Downstream Products

• 143816-71-1 2-<3-<2-(7-chloro-2-quinolinyl)-(E)-ethenyl>phenyl>-1,3-dioxolane 
• 878007-03-5 1-(3-(2-(7-Chloro-2-quinolinyl)ethenyl)phenyl)ethanone 
• 139425-04-0 trans-3-[2-(7-chloroquinolin-2-yl)ethenyl]benzyl alcohol 
• 1095202-12-2 ethyl 3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-hydroxypropanoate 
• 1258428-71-5 trans-1-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(1-hydroxy-1-methylethyl)phenyl]propan-1-one 
• 287930-77-2 (S,E)-1-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propan-1-ol 
• 140640-13-7 (E)-δ-chloro-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzenepentanenitrile 
• 1429879-00-4 7-chloro-2-[(E)-2-(3-oxiranylphenyl)vinyl]quinoline 
• 1429879-29-7 7-chloro-2-[(2E)-2-{3-(3E)-[2-(oxiran-2-yl)vinyl]phenyl}vinyl]quinoline 
• 1429879-27-5 (-)-7-chloro-2-[(E)-2-[3-[(2S)-oxiran-2-yl]phenyl]vinyl]quinoline 
• 1429879-26-4 2-Bromo-1-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-ethanone 
• 1429879-12-8 methyl 2-(2-{3-[(E)-2-(7-chloroquinolin-2-yl)vinyl]phenyl}-2-oxoethylsulfanyl)benzoate 
• 1429875-52-4 2-(2-acetoxy-2-{3-[(E)-2-(7-chloroquinolin-2-yl)vinyl]phenyl}ethylsulfanyl)benzoic acid 
• 1429879-11-7 methyl 2-(2-{3-[(E)-2-(7-chloroquinolin-2-yl)vinyl]phenyl}-2-hydroxyethylsulfanyl)benzoate 

Relevant articles and documents

Direct alkenylation of alkylazaarenes with aldehydes through C(sp3)-H functionalization under catalytic InCl3 activation

Under the influence of InCl3 as a Lewis acid catalyst, a methodology on the C(sp3)-H functionalization of alkylazaarenes has been demonstrated through the activation of benzylic C-H bonds towards their addition reaction with the appropriate electrophiles. This methodology was chiefly applied in the direct alkenylation of primary and secondary benzylic C-H bonds of alkylazaarenes with aldehydes. A variety of alkenyl products were afforded in generally good yields including the starting alkenyl intermediate used in the synthesis of montelukast and other related molecules.

Lewis-acid-catalyzed benzylic reactions of 2-methylazaarenes with aldehydes

Lewis-acid-catalyzed benzylic reactions of 2-methylazaarenes with aldehydes have been investigated. Series of azaarene derivatives were afforded by this reaction. 2-(Pyridin-2-yl)ethanols with common substituents were formed through the LiNTf2-promoted aldol reaction for the first time. 2-Alkenylpyridines, exclusively in the form of the E isomers, were synthesized in the presence of LiNTf2 cooperated with H2NTf. In the presence of La(Pfb)3 as catalysis, 2-alkenylquinolines were obtained in high yields through the reactions between 2-methylquinolines and aldehydes under air.

Cobalt-catalyzed direct alkenylation of 2-methylquinolines with aldehydes via C(sp3)-H functionalization in water

The direct C(sp3)-H alkenylation of 2-methylquinolines with aldehydes as a simple methodology to afford 2-alkenylated quinolines is reported. In the presence of catalytic CoCl2 in water, the economically and ecologically sound transformation is proposed to proceed via the direct benzylic addition to the aldehyde followed by an elimination step to provide 2-alkenylated quinolines in good to excellent yield of up to 95%. Georg Thieme Verlag Stuttgart New York.