Methylamine → 6-bromo-2-(4-fluorophenyl)-N-methyl-2H-indazole-3-carboxamide

HRID 1037563Notes

Reaction equation

HRID 1037563 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]([OH:20])=O.[CH3:21][N:22](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN>CN(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:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[C:6]=2[C:18]([NH:22][CH3:21])=[O:20]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 675127396-bromo-2-(4-fluorophenyl)-2H-indazole-3-carboxylic acid

Product 1

HCID 677756736-bromo-2-(4-fluorophenyl)-N-methyl-2H-indazole-3-carboxamideYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of compound (xvi) (50 mg, 0.15 mmol) in DMF (5 mL) were added HATU (85 mg, 0.22 mmol) DIPEA (0.1 mL, 0.45 mmol) and methyl amine solution (0.26 mL, 0.15 mmol) at 0° C. and the reaction mixture was stirred at RT. After 12 h the reaction mixture was diluted with water and the precipitated solid was filtered to give 6-bromo-2-(4-fluorophenyl)-N-methyl-2H-indazole-3-carboxamide (xvii) (30 mg, 58%) as a white solid. ESI-MS m/z calculated for [M+H]+: 348.01; found: 347.90.

Workup

  1. filtrationthe precipitated solid was filtered

Sources & evidence

ORD record
ord-6eb87dbfc45c4ea7ba00068a0ba414d4
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

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