Dimethylformamide → N-Cyclopropyl-3-(2-(4-hydroxybenzyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-4-methylbenzamide

HRID 907269Notes

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+].BrC[C:29]1[CH:30]=[C:31]([OH:35])[CH:32]=[CH:33][CH:34]=1.[CH3:36]N(C=O)C>>[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])[N:18]([CH2:36][C:34]3[CH:29]=[CH:30][C:31]([OH:35])=[CH:32][CH:33]=3)[CH:17]=[CH:16]4)[CH:7]=2)[CH2:2][CH2:3]1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 24758Sodium hydride

HCID 137401503-(Bromomethyl)phenol

HCID 25020457N-Cyclopropyl-4-methyl-3-(1-oxo-1,2-dihydro-isoquinolin-6-yl)-benzamide

Product 1

HCID 57551752N-Cyclopropyl-3-(2-(4-hydroxybenzyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-4-methylbenzamide

Procedure

To a solution of the product of Example 11 (0.5 g) in DMF (10 mL) was added 60% sodium hydride in mineral oil (0.1 g) and the mixture stirred at room temperature for 1 hour. To this mixture was then added 3-(bromomethyl)phenol (0.4 g) and the mixture stirred at room temperature for 2 hours. The reaction mixture was concentrated to dryness and the residue purified (SiO2 chromatography 9:1 dichloromethane:methanol) to give the sub-title compound (0.33 g).

Workup

concentrationThe reaction mixture was concentrated to dryness
customthe residue purified (SiO2 chromatography 9:1 dichloromethane:methanol)

Sources & evidence

ORD record: ord-cbb0056f22964cf29b004dfb5f67d18d
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012979B2

Reaction notes

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