Sodium Hydroxide → 6-bromo-2-(4-fluorophenyl)-2H-indazole-3-carboxamide

HRID 1037561Notes

Reaction equation

HRID 1037561 reaction equation
[Br:1][C:2]1[CH:3]=[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:19].[OH-:20].[Na+]>C(O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([C:11]1[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=1)[C:6]=2[C:18]([NH2:19])=[O:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 675136096-bromo-2-(4-fluorophenyl)-2H-indazole-3-carbonitrile

Product 1

HCID 677763456-bromo-2-(4-fluorophenyl)-2H-indazole-3-carboxamideYield 94%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred suspension of compound (xiv) (50 mg, 0.16 mmol) in ethanol:water (1:1, 6 mL) was added sodium hydroxide (63 mg, 0.16 mmol) and the reaction mixture was heated at 70° C. for 2 h. The reaction mixture was cooled to RT and the volatiles were removed under reduced pressure. The residue was acidified to pH 2 upon addition of 2N hydrochloric acid. The resulting precipitate was filtered, washed with water (2×20 mL) and dried (Na2SO4) to give 6-bromo-2-(4-fluorophenyl)-2H-indazole-3-carboxamide (xv) (50 mg, 94%) as white solid. ESI-MS m/z calculated for [M+H]+: 334.00; found: 334.00.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customthe volatiles were removed under reduced pressure
  3. additionThe residue was acidified to pH 2 upon addition of 2N hydrochloric acid
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water (2×20 mL)
  6. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-3e865aa87fec43ca92ae29c9324cac40
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

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