Water → 3-(4-fluorophenyl)-1H-indazole-5-carboxamide

HRID 1349609Notes

Reaction equation

HRID 1349609 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](Cl)=[O:14])=[CH:10][CH:11]=2)[C:6]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[N:5]1)(=O)C.[OH-].[NH4+:24].O>C(Cl)Cl>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[C:9]([C:13]([NH2:24])=[O:14])[CH:8]=3)[NH:4][N:5]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 224802271-acetyl-3-(4-fluorophenyl)-1H-indazole-5-carbonyl chloride

Product 1

HCID 99925193-(4-fluorophenyl)-1H-indazole-5-carboxamideYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-acetyl-3-(4-fluorophenyl)-1H-indazole-5-carbonyl chloride (200 mg, 0.63 mmol) in methylene chloride (20 mL) was added saturated ammonium hydroxide (NH4OH). The solution was stirred overnight at room temperature when it was added to water (100 mL) and extracted with ethyl acetate (3×40 mL). The combined organic layers were dried (Na2SO4) and concentrated under vacuo to an oil. The resulting oil was chromatographed on silica gel, eluting with 10% methanol in methylene chloride to give the title compound (115 mg, 72%). 1H NMR (DMSO-d6) δ 13.4 (s, 1H), 8.60 (s, 1H), 8.09 (m, 2H), 7.94 (d, 1H), 7.61 (d, 1H), 7.38 (t, 2H); ES-MS (m/z) 256 [M+1]+.

Workup

  1. extractionextracted with ethyl acetate (3×40 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated under vacuo to an oil
  4. customThe resulting oil was chromatographed on silica gel
  5. washeluting with 10% methanol in methylene chloride

Sources & evidence

ORD record
ord-727ab40707cf4ea98c64d4472e3177af
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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