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

HRID 1272755Notes

Reaction equation

HRID 1272755 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.N1[CH:28]=[CH:27]C=CC=1.[OH-:29].[NH4+].O>C(O)C>[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]([O:29][CH2:27][CH3:28])=[O:14])[CH:8]=3)[NH:4][N:5]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 14923Ammonium HydroxideHCID 224802271-acetyl-3-(4-fluorophenyl)-1H-indazole-5-carbonyl chloride

Product 1

HCID 22479944ethyl 3-(4-fluorophenyl)-1H-indazole-5-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-acetyl-3-(4-fluorophenyl)-1H-indazole-5-carbonyl chloride (100 mg, 0.33 mmol) in ethanol (40 mL) was added pyridine (0.5 mL). The reaction was stirred overnight at room temperature when saturated ammonium hydroxide (1 mL) was added. The reaction was stirred overnight when water (150 mL) was added and the solution filtered. The solid was dried to recover the product (100 mg, 100% yield). 1H NMR (DMSO-d6) δ 13.6 (s, 1H), 8.62 (s, 1H), 8.03–7.9 (m, 3H), 7.70 (d, 1H), 7.61 (d, 1H), 7.42 (t, 2H); ES-MS (m/z) 285 [M+1]+.

Workup

  1. additionwas added
  2. additionwas added
  3. filtrationthe solution filtered
  4. customThe solid was dried

Sources & evidence

ORD record
ord-99838b70129941ccae365370ccbc5100
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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