Sodium hydride → N-Cyclopropyl-3-[1-(cyclopropylmethyl)-1H-indazol-5-yl]-4-methylbenzamide

HRID 1988932Notes

Reaction equation

HRID 1988932 reaction equation
[CH:1]1([NH:4][C:5](=[O:22])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[NH:18][N:17]=[CH:16]4)[CH:7]=2)[CH2:3][CH2:2]1.[H-].[Na+].[CH:25]1([CH2:28]Br)[CH2:27][CH2:26]1>CN(C=O)C.CO>[CH:1]1([NH:4][C:5](=[O:22])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[N:18]([CH2:28][CH:25]3[CH2:27][CH2:26]3)[N:17]=[CH:16]4)[CH:7]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 10469531N-cyclopropyl-3-(1H-indazol-5-yl)-4-methylbenzamide

Product 1

HCID 68677012N-Cyclopropyl-3-[1-(cyclopropylmethyl)-1H-indazol-5-yl]-4-methylbenzamide

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of N-cyclopropyl-3-(1H-indazol-5-yl)-4-methylbenzamide (Example 17) (0.10 g) in dry DMF (3 ml) was treated with sodium hydride (60% oil dispersion, 0.017 g) under nitrogen. After 5 min cyclopropylmethyl bromide (0.04 ml) was added and the yellow solution was stirred at room temp. for 18 h. Methanol (2 drops) was added and the solvent was evaporated. The residue was purified by column chromatography on silica eluting with cyclohexane:ethyl acetate (2:1 to 1:1) to give the title compound (0.05 g).

Workup

  1. customthe solvent was evaporated
  2. customThe residue was purified by column chromatography on silica eluting with cyclohexane:ethyl acetate (2:1 to 1:1)

Sources & evidence

ORD record
ord-b761f55fce55439eb27b4cfc2d832076
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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