Cesium carbonate → HCID 22265310, compound

HRID 489177Notes

Reaction equation

HRID 489177 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])=[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:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([CH2:17][C:16]3[CH:19]=[CH:20][CH:21]=[C:14]([F:13])[CH:15]=3)[C:9]2=[O:12])=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 680073-Fluorobenzyl bromideHCID 178517691HCID 178517691, compound

Product 1

HCID 22265310HCID 22265310, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The alkylation of 7-bromo-1-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-1-one

Workup

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

Sources & evidence

ORD record
ord-91bf0d151d5b4c599356f296f4cc3245
Source dataset
uspto-grants-2005_12
Patent number
US06977261B2

Reaction notes

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