Sodium hydride → 3-(2-((6-Bromopyridin-3-yl)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-N-cyclopropyl-4-methylbenzamide

HRID 907264Notes

Reaction equation

HRID 907264 reaction equation
[CH:1]1([NH:4][C:5](=[O:24])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[NH:18][CH:17]=[CH:16]4)[CH:7]=2)[CH2:3][CH2:2]1.[H-].[Na+].[Br:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34]Br)=[CH:30][N:29]=1>CN(C=O)C>[Br:27][C:28]1[N:29]=[CH:30][C:31]([CH2:34][N:18]2[CH:17]=[CH:16][C:15]3[C:20](=[CH:21][CH:22]=[C:13]([C:8]4[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=4[CH3:12])[C:5]([NH:4][CH:1]4[CH2:2][CH2:3]4)=[O:24])[CH:14]=3)[C:19]2=[O:23])=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 64246602-Bromo-5-bromomethylpyridineHCID 25020457N-Cyclopropyl-4-methyl-3-(1-oxo-1,2-dihydro-isoquinolin-6-yl)-benzamide

Product 1

HCID 575517913-(2-((6-Bromopyridin-3-yl)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-N-cyclopropyl-4-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of the product of Example 11 (400 mg) in DMF (5 mL) was added sodium hydride (60 mg) and the reaction stirred at room temperature for 10 minutes before the addition of a solution of 2-bromo-5-(bromomethyl)pyridine (760 mg) in DMF (5 mL). The reaction mixture was stirred at room temperature for 30 min.

Sources & evidence

ORD record
ord-b846acf16a9648ed95c514834a761eb2
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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