Cesium carbonate → HCID 22265296, compound

HRID 489183Notes

Reaction equation

HRID 489183 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])=[CH:4][N:3]=1.[F:13][C:14]([F:24])([F:23])[C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18]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]=[N:7][N:8]([CH2:18][C:17]3[CH:20]=[CH:21][CH:22]=[C:15]([C:14]([F:13])([F:23])[F:24])[CH:16]=3)[C:9]2=[O:12])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 178518908HCID 178518908, compound

Product 1

HCID 22265296HCID 22265296, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The alkylation of 7-bromo-1-hydroxy-3,6-diazaisoquinoline (1.00 g, 4.46 mmol) using 3-trifluoromethyl-benzyl bromide (1.60 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): 7-(3-phenylprop-1-ynyl)-2-(3-trifluoromethylbenzyl)-2H-3,6-diazaisoquinolin-1-one

Workup

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

Sources & evidence

ORD record
ord-42cf653c8d2a4191be4edcd2c2e60a68
Source dataset
uspto-grants-2005_12
Patent number
US06977261B2

Reaction notes

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