Cesium carbonate → HCID 22265327, compound

HRID 489184Notes

Reaction equation

HRID 489184 reaction equation
[Br:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[N:7][N:8]=[C:9]2[OH:12])=[CH:4][CH:3]=1.[Cl: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[N:11]=[C:10]2[C:5]([CH:6]=[N:7][N:8]([CH2:17][C:16]3[CH:19]=[CH:20][CH:21]=[C:14]([Cl:13])[CH:15]=3)[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 178518888HCID 178518888, compound

Product 1

HCID 22265327HCID 22265327, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The alkylation of 7-bromo-1-hydroxy-3,8-diazaisoquinoline (1.00 g, 4.46 mmol) using 3-Chlorobenzyl bromide (1.37 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). Trituration with hexanes/ethyl acetate 10:1 will afford the desired product. Step 2): 2-(3-chlorobenzyl)-7-(3-phenylprop-1-ynyl)-2H-3,8-diazaisoquinolin-1-one

Sources & evidence

ORD record
ord-4fa213e0784d4c7888088257d500e926
Source dataset
uspto-grants-2005_12
Patent number
US06977261B2

Reaction notes

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