4498-67-3

Basic information

• Product Name: Indazole-3-carboxylic acid
• Synonyms: 1H-INDAZOL-3-CARBONIC ACID;1H-INDAZOLE-3-CARBOXYLIC ACID;1H-INDAZOLE-3-CARBONIC ACID;AKOS BB-9978;3-INDAZOLECARBOXYLIC ACID;3-CARBOXYINDAZOLE;ndazole-3-carboxylic acid;INDAZOLE-3-CARBOXYLIC ACID
• CAS NO: 4498-67-3
• Molecular Formula: C₈H₆N₂O₂
• Molecular Weight: 162.15
• EINECS: 224-794-5
• Product Categories: PHARMACEUTICAL INTERMEDIATES;Acids and Derivatives;Heterocycles;Indoles and derivatives;pharmacetical;Carboxylic Acids;Organic acids;(intermediate of granisetron);Indazoles;Indole Derivatives;Carboxylic Acids;Fused Ring Systems;Building Blocks;Heterocyclic Building Blocks
• Mol File: 4498-67-3.mol
• Article Data: 27

Chemical Properties

• Melting Point: 266-270 °C (dec.)
• Boiling Point: 443.7 °C at 760 mmHg
• Flash Point: 222.2 °C
• Appearance: beige/powder
• Density: 1.506 g/cm³
• Vapor Pressure: 1.18E-08mmHg at 25°C
• Refractive Index: 1.743
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.03±0.10(Predicted)
• BRN: 6354
• CAS DataBase Reference: Indazole-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Indazole-3-carboxylic acid(4498-67-3)
• EPA Substance Registry System: Indazole-3-carboxylic acid(4498-67-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36-36/37/38
• Safety Statements: 26-36/37/39-22
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 4498-67-3(Hazardous Substances Data)

Usage

Chemical Properties

yellow crystal

Uses

Different sources of media describe the Uses of 4498-67-3 differently. You can refer to the following data:
1. Indazole-3-carboxylic acid is indole derivatives useful in treatment of pain and inflammation
2. Indazole-3-carboxylic acid may be used in the synthesis of the following:N-(8-methyl-azabicyclo[3.2.11]oct-3-yl)-1H-indazole-3-carboxamideN-(1- benzyl-4-methylhexahydro-1H-1,4-diazepin-6-yl)-1H-indazole-3-carboxamide1H-indazole-3-carboxamide

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 26, p. 531, 1989 DOI: 10.1002/jhet.5570260251

InChI:InChI=1/C8H6N2O2/c11-8(12)7-5-3-1-2-4-6(5)9-10-7/h1-4H,(H,9,10)(H,11,12)

Synthetic route

indole-2,3-dione (91-56-5) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
Stage #1: indole-2,3-dione With sodium hydroxide In water at 20 - 50℃; for 1.5h; Stage #2: With sulfuric acid; sodium nitrite In water at 0℃; for 1h; Stage #3: With hydrogenchloride; tin(ll) chloride In water for 1.16667h;	100%
With sodium hydroxide; sulfuric acid; sulfur dioxide; sodium nitrite Reagens 4: Zinnchloruer;
With sulfuric acid; sodium nitrite danach SnCl2;

methyl 1-acetylindazole-3-carboxylate (186966-06-3) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
With sodium hydroxide In hydrogenchloride; water	100%
With sodium hydroxide; water for 1.5h; Heating;	97%

ethyl 1-acetyl-1H-indazole-3-carboxylate (78155-12-1) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
With sodium hydroxide; water for 1.5h; Heating;	98%

1-(3-(morpholine-4-carbonyl)-1H-indazol-1-yl)ethanone (186966-03-0) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
With sodium hydroxide; water for 3h; Heating;	96%

4-bromobenzylideneaminoisatine (1630015-70-1) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
Stage #1: 4-bromobenzylideneaminoisatine With hydrogenchloride In water; acetic acid at 90 - 100℃; for 1h; Stage #2: With acetic acid at 115℃; for 1h;	85%

1-(benzylideneamino)indoline-2,3-dione (10604-20-3) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
With hydrogenchloride; acetic acid In dichloromethane; ISOPROPYLAMIDE; water at 15 - 90℃; Product distribution / selectivity; Reflux; Inert atmosphere;	76%
Stage #1: 1-(benzylideneamino)indoline-2,3-dione With hydrogenchloride; acetic acid In water at 90℃; for 1h; Stage #2: With acetic acid at 115℃; for 0.5h;	71%

3-(hydroxymethyl)-1H-indazole (64132-13-4) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
With chromium(VI) oxide; sulfuric acid In acetone at 20℃; for 24h;	64%
With chromium(VI) oxide; sulfuric acid In acetone at 20℃; for 24h;	64%

tin(II)chloride dihydrate + indole-2,3-dione (91-56-5) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
With sodium hydroxide; sulfuric acid; sodium nitrite In hydrogenchloride; water	31%

1-dimethylamino-indolin-2-one (861798-91-6) + 2,3-dimethyl-4-nitroso-aniline (871876-73-2) + sodium ethanolate (141-52-6) → 1H-Indazole-3-carboxylic acid (4498-67-3)

1-benzylideneamino-indole-2,3-dione (10604-20-3) + acetic acid (64-19-7) → benzaldehyde (100-52-7) + 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
mit Wasserdampf;

indazole-3-carbonitrile (50264-88-5) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
With hydrogenchloride

N-acetylaminoisatin (123704-99-4) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
With sulfuric acid for 2.5h; Heating;

sulfuric acid (7664-93-9) + 1-acetylamino-indoline-2,3-dione-3-oxime → 1H-Indazole-3-carboxylic acid (4498-67-3)

N-acetylamino-isatin-β oxime → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
With sulfuric acid

N-benzylidenamino-isatin → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
With hydrogenchloride

hydrogenchloride (7647-01-0) + 1-benzylideneamino-indole-2,3-dione (10604-20-3) → benzaldehyde (100-52-7) + 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
mit Wasserdampf;

oxalic acid-(benzylidene-phenyl-hydrazide)-chloride (109411-83-8) → 1H-Indazole-3-carboxylic acid (4498-67-3) + N-benzylidenamino-isatin

Conditions	Yield
With carbon disulfide; aluminium trichloride

2-(2-nitrophenyl)acetic acid (3740-52-1) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / cc. H2SO4 / 4 h / Heating 2: 97 percent / H2 / 5percent Pd/C / toluene / Ambient temperature 3: 87 percent / 90percent t-BuONO / acetic acid / 0.5 h / 90 - 95 °C 4: 97 percent / NaOH, water / 1.5 h / Heating View Scheme
Multi-step reaction with 4 steps 1: 94 percent / cc. H2SO4 / 4 h / Heating 2: 97 percent / H2 / 5percent Pd/C / toluene / Ambient temperature 3: 83 percent / 90percent t-BuONO / toluene / 0.5 h / 90 - 95 °C 4: 98 percent / NaOH, water / 1.5 h / Heating View Scheme
Multi-step reaction with 4 steps 1: 89 percent / SOCl2 / dimethylformamide; 1,2-dichloro-ethane / 35-40 deg C, 2 h then 20 deg C, 2 h 2: 95 percent / H2 / 5percent Pd/C / toluene / Ambient temperature 3: 76 percent / 90percent t-BuONO / toluene / 0.5 h / 90 - 95 °C 4: 96 percent / NaOH, water / 3 h / Heating View Scheme
Multi-step reaction with 5 steps 1: 89 percent / SOCl2 / dimethylformamide; 1,2-dichloro-ethane / 35-40 deg C, 2 h then 20 deg C, 2 h 2: 92 percent / Fe, aq. NH4Cl / propan-2-ol / 1 h / Heating 3: toluene / rt to 95 deg C 4: 76 percent / 90percent t-BuONO / toluene / 0.5 h / 90 - 95 °C 5: 96 percent / NaOH, water / 3 h / Heating View Scheme

methyl (2-nitrophenyl)acetate (30095-98-8) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / H2 / 5percent Pd/C / toluene / Ambient temperature 2: 87 percent / 90percent t-BuONO / acetic acid / 0.5 h / 90 - 95 °C 3: 97 percent / NaOH, water / 1.5 h / Heating View Scheme

ethyl 2-nitrophenylacetate (31912-02-4) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / H2 / 5percent Pd/C / toluene / Ambient temperature 2: 83 percent / 90percent t-BuONO / toluene / 0.5 h / 90 - 95 °C 3: 98 percent / NaOH, water / 1.5 h / Heating View Scheme

(2-acetylamino-phenyl)-acetic acid ethyl ester (186966-08-5) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 83 percent / 90percent t-BuONO / toluene / 0.5 h / 90 - 95 °C 2: 98 percent / NaOH, water / 1.5 h / Heating View Scheme

methyl 3-(2-acetamidophenyl)propanoate (134810-89-2) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / 90percent t-BuONO / acetic acid / 0.5 h / 90 - 95 °C 2: 97 percent / NaOH, water / 1.5 h / Heating View Scheme

4-[(2-nitro-phenyl)-acetyl]-morpholine (25888-16-8) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / H2 / 5percent Pd/C / toluene / Ambient temperature 2: 76 percent / 90percent t-BuONO / toluene / 0.5 h / 90 - 95 °C 3: 96 percent / NaOH, water / 3 h / Heating View Scheme
Multi-step reaction with 4 steps 1: 92 percent / Fe, aq. NH4Cl / propan-2-ol / 1 h / Heating 2: toluene / rt to 95 deg C 3: 76 percent / 90percent t-BuONO / toluene / 0.5 h / 90 - 95 °C 4: 96 percent / NaOH, water / 3 h / Heating View Scheme

4-(2-aminophenylacetyl)morpholine (80798-83-0) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene / rt to 95 deg C 2: 76 percent / 90percent t-BuONO / toluene / 0.5 h / 90 - 95 °C 3: 96 percent / NaOH, water / 3 h / Heating View Scheme

N-[2-(2-Morpholin-4-yl-2-oxo-ethyl)-phenyl]-acetamide (186966-07-4) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / 90percent t-BuONO / toluene / 0.5 h / 90 - 95 °C 2: 96 percent / NaOH, water / 3 h / Heating View Scheme

N-Acetylaminoisonitrosoacetanilide (123704-98-3) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 96percent H2SO4 / 0.25 h / 85 °C 2: aq. H2SO4 / 2.5 h / Heating View Scheme

1-acetyl-2-phenylhydrazine (114-83-0) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 79 percent / hydroxylamine hydrochloride, sodium sulphate, 1 N HCl / H2O / 0.17 h / 100 °C 2: 96percent H2SO4 / 0.25 h / 85 °C 3: aq. H2SO4 / 2.5 h / Heating View Scheme

2-nitro-benzeneacetonitrile (610-66-2) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: tin; hydrochloric acid 2: acid; sodium nitrite 3: concentrated hydrochloric acid View Scheme

2-aminophenylacetonitrile (2973-50-4) → 1H-Indazole-3-carboxylic acid (4498-67-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: acid; sodium nitrite 2: concentrated hydrochloric acid View Scheme

p-toluidine (106-49-0) + 1H-Indazole-3-carboxylic acid (4498-67-3) → N-(p-tolyl)-1H-indazole-3-carboxamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃;	100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃; for 10h;	66%

1H-Indazole-3-carboxylic acid (4498-67-3) + 4-methoxycarbonyl aniline (619-45-4) → methyl 4-(1H-indazole-3-carboxamido)benzoate

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃;	100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃; for 10h;	10%

4-chloro-aniline (106-47-8) + 1H-Indazole-3-carboxylic acid (4498-67-3) → N-(4-chlorophenyl)-1H-indazole-3-carboxamide (23707-00-8)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃;	100%

methanol (67-56-1) + 1H-Indazole-3-carboxylic acid (4498-67-3) → methyl 1H-indazole-3-carboxylate (43120-28-1)

Conditions	Yield
With sulfuric acid for 2h; Heating;	98%
With sulfuric acid for 2h; Reflux;	95%
With thionyl chloride for 3h; Reflux;	95%

5,6-diamino-1-ethyl-3,3-dimethylindol-2-one (881693-01-2) + 1H-Indazole-3-carboxylic acid (4498-67-3) → 5-ethyl-2-(1H-indazol-3-yl)-7,7-dimethyl-5,7-dihydro-3H-imidazo[4,5-f]indol-6-one

Conditions	Yield
Stage #1: 5,6-diamino-1-ethyl-3,3-dimethylindol-2-one; 1H-Indazole-3-carboxylic acid With PPA; phosphorus pentoxide at 150℃; for 6h; Stage #2: With ammonia In water pH=7 - 8;	97%

endo-9-methyl-9-azabicyclo[3.3.1]nonan-3-amine (76272-41-8, 141650-55-7, 76272-56-5) + 1H-Indazole-3-carboxylic acid (4498-67-3) → endo-N-(9-methyl-9-azabicyclo<3.3.1>nonan-3-yl)-1H-indazole-3-carboxamide (107007-95-4)

Conditions	Yield
Stage #1: 1H-Indazole-3-carboxylic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: endo-9-methyl-9-azabicyclo[3.3.1]nonan-3-amine In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere;	97%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 20℃;	73%

1H-Indazole-3-carboxylic acid (4498-67-3) + dimethyl sulfate (77-78-1) → methyl 1H-indazole-3-carboxylate (43120-28-1)

Conditions	Yield
Stage #1: 1H-Indazole-3-carboxylic acid With potassium carbonate In acetone at 20℃; for 0.166667h; Stage #2: dimethyl sulfate In acetone for 4h; Reflux;	95%

Phenylpropargyl aldehyde (2579-22-8) + Benzyl isocyanide (88333-03-3, 10340-91-7) + 1H-Indazole-3-carboxylic acid (4498-67-3) + 4-bromo-aniline (106-40-1) → N,4-dibenzyl-2-(4-bromophenyl)-1-oxo-1,2-dihydropyrazino[1,2-b]indazole-3-carboxamide

Conditions	Yield
Stage #1: Phenylpropargyl aldehyde; 4-bromo-aniline In 2,2,2-trifluoroethanol at 20℃; for 0.166667h; Microwave irradiation; Stage #2: Benzyl isocyanide; 1H-Indazole-3-carboxylic acid In N,N-dimethyl-formamide at 20 - 110℃; Microwave irradiation;	95%

oxetan-3-yl-methylamine (952182-03-5) + 1H-Indazole-3-carboxylic acid (4498-67-3) → N-methyl-N-(oxetan-3-yl)-1H-indazole-3-carboxamide

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 24h; Reagent/catalyst; Temperature; Solvent;	94%

1H-Indazole-3-carboxylic acid (4498-67-3) + methylamine (74-89-5) → 1-methyl-3-indolecarboxylic acid (32387-21-6)

Conditions	Yield
Stage #1: 1H-Indazole-3-carboxylic acid With tin(ll) chloride In acetonitrile at 55℃; for 6h; Stage #2: methylamine In acetonitrile at 9℃; for 41h; Temperature; Reflux;	93%

tert-butyl [2-amino-2-(hydroxyimino)ethyl]carbamate (479079-15-7, 479080-20-1) + 1H-Indazole-3-carboxylic acid (4498-67-3) → tert-butyl 2-(1H-indazole-3-carbonyloxyimino)-2-aminoethylcarbamate (1151512-97-8)

Conditions	Yield
Stage #1: 1H-Indazole-3-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: tert-butyl 2-amino-2-(hydroxyimino)ethylcarbamate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;	92%
Stage #1: 1H-Indazole-3-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: tert-butyl 2-amino-2-(hydroxyimino)ethylcarbamate In N,N-dimethyl-formamide at 20℃;	92%

1H-Indazole-3-carboxylic acid (4498-67-3) → 1H-indazole-3-carbonyl chloride (72083-74-0)

Conditions	Yield
With thionyl chloride at 20℃; for 2h; Inert atmosphere;	91%
With thionyl chloride for 1h; Reflux;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 2h;
With thionyl chloride for 8h; Reflux;
With thionyl chloride at 80℃; for 4h;

1H-Indazole-3-carboxylic acid (4498-67-3) + dimethyl sulfate (77-78-1) → 1-methylindazole-3-carboxylic acid hydrochloride

Conditions	Yield
Stage #1: 1H-Indazole-3-carboxylic acid With calcium methylate In methanol for 2h; Heating / reflux; Stage #2: dimethyl sulfate In methanol for 3h; Heating / reflux; Stage #3: With hydrogenchloride In water for 2h; pH=1;	87.7%

1H-Indazole-3-carboxylic acid (4498-67-3) → 5-bromobenzopyrazole-3-carboxylic acid (1077-94-7)

Conditions	Yield
With bromine; acetic acid at 90 - 120℃; for 16h;	87.5%
Stage #1: 1H-Indazole-3-carboxylic acid With acetic acid at 120℃; Stage #2: With bromine; acetic acid at 90℃; for 16h;	87.5%
With bromine; acetic acid at 90 - 120℃; for 16h;	87.5%

1H-Indazole-3-carboxylic acid (4498-67-3) + dimethyl sulfate (77-78-1) → 1-methyl-1H-indazole-3-carboxylic acid (50890-83-0)

Conditions	Yield
Stage #1: 1H-Indazole-3-carboxylic acid With calcium oxide In methanol for 2h; Heating / reflux; Stage #2: dimethyl sulfate In methanol for 4h; Heating / reflux;	85.6%
Stage #1: 1H-Indazole-3-carboxylic acid With magnesium n-propylate In propan-1-ol for 2h; Heating / reflux; Stage #2: dimethyl sulfate In propan-1-ol at 20℃; for 5h; Heating / reflux;	83.8%
Stage #1: 1H-Indazole-3-carboxylic acid With magnesium ethylate In propan-1-ol for 2h; Heating / reflux; Stage #2: dimethyl sulfate In propan-1-ol at 20℃; for 2h; Heating / reflux;	79.2%
Stage #1: 1H-Indazole-3-carboxylic acid With barium(II) oxide In propan-1-ol for 2h; Heating / reflux; Stage #2: dimethyl sulfate In propan-1-ol at 20℃; for 2h; Heating / reflux;	65.4%

4-amino-1-benzylpiperidine (50541-93-0) + 1H-Indazole-3-carboxylic acid (4498-67-3) → N-(1-benzylpiperidin-4-yl)-1H-indazole-3-carboxamide (207296-87-5)

Conditions	Yield
Stage #1: 1H-Indazole-3-carboxylic acid With 1,1'-carbonyldiimidazole In DMF (N,N-dimethyl-formamide) at 60℃; for 2h; Stage #2: 4-amino-1-benzylpiperidine In DMF (N,N-dimethyl-formamide) at 60℃; for 2h;	85.1%
With 1,1'-carbonyldiimidazole 1.) DMF, 60 deg C, 2 h, 2.) DMF, 60 deg C, 2 h; Yield given. Multistep reaction;
In N-methyl-acetamide; dichloromethane; 1,1'-carbonyldiimidazole	76%.

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + 1H-Indazole-3-carboxylic acid (4498-67-3) → 1H-indazole-3-carboxylic acid methoxy(methyl)amide (351457-12-0)

Conditions	Yield
Stage #1: N,O-dimethylhydroxylamine*hydrochloride; 1H-Indazole-3-carboxylic acid With pyridine In tetrahydrofuran at 20℃; for 3h; Cooling with ice; Stage #2: With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃;	85%
With pyridine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In tetrahydrofuran at 0 - 20℃; for 13.5h;	84%
Stage #1: N,O-dimethylhydroxylamine*hydrochloride; 1H-Indazole-3-carboxylic acid With pyridine In tetrahydrofuran at 0 - 20℃; for 2.5h; Stage #2: With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃;	84%

1H-Indazole-3-carboxylic acid (4498-67-3) → methyl 1H-indazole-3-carboxylate (43120-28-1)

Conditions	Yield
Stage #1: methanol With acetyl chloride at 0℃; for 0.166667h; Stage #2: 1H-Indazole-3-carboxylic acid at 0 - 20℃;	85%
With sodium bicarbonate; sulfuric acid In methanol	61%
In methanol

oxotribromobis(triphenylphosphine)rhenium(V) (18703-07-6, 74741-94-9, 162117-95-5) + 1H-Indazole-3-carboxylic acid (4498-67-3) → [ReO(bromide)2(indazole-3-carboxylate)(triphenylphosphine)]*(triphenylphosphine oxide)

Conditions	Yield
With air In tetrahydrofuran byproducts: HBr, P(C6H5)3; addn. of Re complex to N compd. (1:1) in C4H8O, heating under reflux for4 h; concn., cooling to room temp., slow diffusion of diethyl ether, isolation of crystals, elem. anal.;	85%

1H-Indazole-3-carboxylic acid (4498-67-3) → 1H-indazole-3-carboxamide (90004-04-9)

Conditions	Yield
Stage #1: 1H-Indazole-3-carboxylic acid With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20℃; for 2h; Inert atmosphere; Stage #2: With ammonia In tetrahydrofuran; water at 20℃; for 1h;	85%
Stage #1: 1H-Indazole-3-carboxylic acid With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20℃; for 2h; Inert atmosphere; Stage #2: With ammonia In tetrahydrofuran; water at 20℃; for 1h; Inert atmosphere;	85%
Stage #1: 1H-Indazole-3-carboxylic acid With thionyl chloride for 3h; Inert atmosphere; Reflux; Stage #2: With ammonia In tetrahydrofuran; water at 20℃; for 0.5h; Inert atmosphere;	76%

1H-Indazole-3-carboxylic acid (4498-67-3) + methyl iodide (74-88-4) → 1-methyl-1H-indazole-3-carboxylic acid (50890-83-0)

Conditions	Yield
Stage #1: 1H-Indazole-3-carboxylic acid With calcium oxide In methanol for 2h; Heating / reflux; Stage #2: methyl iodide In methanol at 20℃; for 26h; Heating / reflux;	83.8%
With hydrogenchloride; sodium chloride; sodium hydrogencarbonate In dimethyl sulfoxide; mineral oil

2-methoxy-phenylamine (90-04-0) + 1H-Indazole-3-carboxylic acid (4498-67-3) → N-(2-methoxyphenyl)-1H-indazole-3-carboxamide (23707-04-2)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃; for 10h;	82%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃;	70%

1H-Indazole-3-carboxylic acid (4498-67-3) + 4-amino-5-(4-methoxyphenyl)-4H-1,2,4-triazole-3-thiol (36209-49-1) → 3-[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-yl]-1H-indazole

Conditions	Yield
With trichlorophosphate at 90 - 95℃;	82%

aniline (62-53-3) + 1H-Indazole-3-carboxylic acid (4498-67-3) → 1H-indazole-3-carboxylic acid phenylamide (23706-99-2)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃;	81%
Stage #1: 1H-Indazole-3-carboxylic acid With thionyl chloride for 3h; Inert atmosphere; Reflux; Stage #2: aniline In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;	70%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 48h;	64%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃; for 10h;	59%

1H-Indazole-3-carboxylic acid (4498-67-3) + (±)-(1R,3r,5S)-9-benzyl-9-azabicyclo[3.3.1]nonan-3-yl acetate (76272-58-7) → N-[(3-endo)-9-(phenylmethyl)-9-azabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide (1210745-16-6)

Conditions	Yield
Stage #1: 1H-Indazole-3-carboxylic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: (±)-(1R,3r,5S)-9-benzyl-9-azabicyclo[3.3.1]nonan-3-yl acetate In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere;	81%

Upstream product

• 7772-99-8 STANNOUS CHLORIDE 
• 10025-69-1 Stannous chloride dihydrate 
• 91-56-5 Isatin 

Downstream Products

• 50264-69-2 Lonidamine 

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