Cesium carbonate → HCID 22268259, compound

HRID 488775Notes

Reaction equation

HRID 488775 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([OH:12])[N:8]=[CH:9]2)=[N:4][CH:3]=1.[F:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][N:8]([CH2:17][C:16]1[CH:19]=[CH:20][CH:21]=[C:14]([F:13])[CH:15]=1)[C:7](=[O:12])[CH:6]=2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 680073-Fluorobenzyl bromideHCID 178515401HCID 178515401, compound

Product 1

HCID 22268259HCID 22268259, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The alkylation of 7-bromo-3-hydroxy-5-azaisoquinoline (1.00 g, 4.40 mmol) using 3-fluorobenzyl bromide (1.27 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): 2-(3-fluorobenzyl)-7-(3-phenyl-prop-1-ynyl)-2H-5-azaisoquinolin-3-one

Workup

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

Sources & evidence

ORD record
ord-6220e42c957040cf984c9e215992230c
Source dataset
uspto-grants-2005_12
Patent number
US06974822B2

Reaction notes

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