5-cyclopropyl-N-methyl-6-[(methylsulfonyl)amino]-2-[4-(prop-1-en-2-yl)phenyl]-2H-indazole-3-carboxamide → 5-cyclopropyl-N-methyl-6-[(methylsulfonyl)amino]-2-[4-(propan-2-yl)phenyl]-2H-indazole-3-carboxamide

HRID 1037538Notes

Reaction equation

HRID 1037538 reaction equation
[CH:1]1([C:4]2[C:12]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:11][C:10]3[C:6](=[C:7]([C:27]([NH:29][CH3:30])=[O:28])[N:8]([C:18]4[CH:23]=[CH:22][C:21]([C:24]([CH3:26])=[CH2:25])=[CH:20][CH:19]=4)[N:9]=3)[CH:5]=2)[CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([C:4]2[C:12]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:11][C:10]3[C:6](=[C:7]([C:27]([NH:29][CH3:30])=[O:28])[N:8]([C:18]4[CH:23]=[CH:22][C:21]([CH:24]([CH3:26])[CH3:25])=[CH:20][CH:19]=4)[N:9]=3)[CH:5]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 675126445-cyclopropyl-N-methyl-6-[(methylsulfonyl)amino]-2-[4-(prop-1-en-2-yl)phenyl]-2H-indazole-3-carboxamide

Product 1

HCID 692493885-cyclopropyl-N-methyl-6-[(methylsulfonyl)amino]-2-[4-(propan-2-yl)phenyl]-2H-indazole-3-carboxamideYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of compound (ii) (10 mg, 0.024 mmol) in MeOH (1 mL) was added 10% palladium on carbon (7 mg). The reaction was stirred vigorously under an atmosphere of hydrogen at RT for 2 h. The reaction mixture was filtered to give 5-cyclopropyl-N-methyl-6-[(methylsulfonyl)amino]-2-[4-(propan-2-yl)phenyl]-2H-indazole-3-carboxamide (iii) as a white solid (10 mg, 99%).

Workup

  1. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-551d4f7b4aa14284a1552d5def205b57
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

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