Cesium carbonate → 7-bromo-2-(4-fluorobenzyl)-2H-3,5-diazaisoquinolin-1-one

HRID 489182Notes

Reaction equation

HRID 489182 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[N:7][N:8]=[C:9]2[OH:12])=[N:4][CH:3]=1.C[CH:14](Br)[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[N:7][N:8]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:9]2=[O:12])=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 133890301-(1-Bromoethyl)-4-fluorobenzeneHCID 178518911HCID 178518911, compound

Product 1

HCID 222653127-bromo-2-(4-fluorobenzyl)-2H-3,5-diazaisoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The alkylation of 7-bromo-1-hydroxy-3,5-diazaisoquinoline (1.00 g, 4.46 mmol) using methyl 4-fluoro-benzyl bromide (1.27 g, 6.69 mmol) and cesium carbonate (2.18 g, 6.69 mmol) in dimethyl-formamide 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-(4-fluorobenzyl)-7-3-phenylprop-1-ynyl-2H-3,5-diazaisoquinolin-1-one

Workup

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

Sources & evidence

ORD record
ord-9b1d2766adac4a1d82138d188421cc6f
Source dataset
uspto-grants-2005_12
Patent number
US06977261B2

Reaction notes

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