Sodium hydride → HCID 66807414, compound

HRID 1843898Notes

Reaction equation

HRID 1843898 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][C:18]=3[CH3:19])[C:9]2=[O:12])=[CH:4][CH:3]=1.Br[CH2:21][CH:22]1[CH2:24][CH2:23]1.[H-].[Na+]>CN(C=O)C>[CH:22]1([CH2:21][O:1][C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][N:8]([C:13]4[CH:14]=[N:15][CH:16]=[CH:17][C:18]=4[CH3:19])[C:9]3=[O:12])=[CH:4][CH:3]=2)[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 56942892HCID 56942892, compound

Product 1

HCID 66807414HCID 66807414, compoundYield 413.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-hydroxy-2-(4-methyl-pyridin-3-yl)-3,4-dihydro-2H-isoquinolin-1-one (27A: 50 mg, 0.196 mmol) was reacted with bromomethyl-cyclopropane (32 mg, 0.236 mmol) and 60% NaH (10 mg, 0.236 mmol) in DMF (2 mL) to afford the crude product. Purification by column chromatography on silica gel (15% ethylacetate in hexane) afforded 250 mg of the product (50% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (15% ethylacetate in hexane)

Sources & evidence

ORD record
ord-3ab81d87c0d84d6fbcfc77eaf8e58f30
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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