Hydrochloric Acid → 6-amino-5-bromo-2-(4-fluorophenyl)-2H-indazole-3-carboxylic acid

HRID 595702Notes

Reaction equation

HRID 595702 reaction equation
[NH2:1][C:2]1[C:3]([Br:20])=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[C:6]=2[C:18]#N.[OH2:21].Cl.[OH-:23].[Na+]>>[NH2:1][C:2]1[C:3]([Br:20])=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[C:6]=2[C:18]([OH:23])=[O:21]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 903324396-amino-5-bromo-2-(4-fluorophenyl)-2H-indazole-3-carbonitrile

Product 1

HCID 903325166-amino-5-bromo-2-(4-fluorophenyl)-2H-indazole-3-carboxylic acidYield 85%

Conditions

Temperature
100 °C

Procedure

A suspension of 6-amino-5-bromo-2-(4-fluorophenyl)-2H-indazole-3-carbonitrile (50 mg, 0.14 mmol) in 10% NaOH (5 mL) was heated at 100° C. for 48 h. The reaction mixture was cooled to RT and poured into water (10 mL). After pH was adjusted to 4 with 1 N HCl, the mixture was extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4, filtered and evaporated to get 6-amino-5-bromo-2-(4-fluorophenyl)-2H-indazole-3-carboxylic acid (45 mg, yield: 85%). 1H-NMR (DMSO-d6, 400 MHz) δ 8.20 (s, 1H), 7.77˜7.82 (m, 2H), 7.45˜7.52 (m, 2H), 7.03 (s, 1H), 6.61 (s, 1H), 5.60 (s, 2H). MS (M+H)+: 350/352.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-b049edf44a5a4d9b87609a60b4a7a962
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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