Cesium carbonate → 3-(7-bromo-1-oxo-1H-6-azaisoquinolin-2-ylmethyl)benzonitrile

HRID 489178Notes

Reaction equation

HRID 489178 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[OH:12])=[CH:4][N:3]=1.[C:13]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18]Br)#[N:14].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([CH2:18][C:17]3[CH:16]=[C:15]([CH:22]=[CH:21][CH:20]=3)[C:13]#[N:14])[C:9]2=[O:12])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 178517684HCID 178517684, compound

Product 1

HCID 222653013-(7-bromo-1-oxo-1H-6-azaisoquinolin-2-ylmethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The alkylation of 7-bromo-1-hydroxy-6-azaisoquinoline (1.00 g, 4.40 mmol) using 3-cyanobenzyl bromide (1.31 g, 6.69 mmol) and cesium carbonate (2.18 g, 6.69 mmol) in dimethylformamide is carried out as previously described in Example 1, Step (1). Purification on a silica gel column eluted with hexanes/ethyl acetate 3:1, followed by trituration with hexanes/ethyl acetate 4:1 will afford the desired product. Step (2): 3-[1-oxo-7-(3-Phenyl-prop-1-ynyl)-1H-6-azaisoquinolin-2-ylmethyl]benzonitrile

Workup

  1. customPurification on a silica gel column
  2. washeluted with hexanes/ethyl acetate 3:1

Sources & evidence

ORD record
ord-92b4c8eb2869404ab131460d5e63a10b
Source dataset
uspto-grants-2005_12
Patent number
US06977261B2

Reaction notes

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