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

HRID 2183116Notes

Reaction equation

HRID 2183116 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-2fb4b10d2553458ab71e93fd2c97d148
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

Loading…