Cesium carbonate → HCID 86591200, compound

HRID 489181Notes

Reaction equation

HRID 489181 reaction equation
[Br:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[OH:12])=[CH:4][CH:3]=1.Br[CH2:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18]([O:20][CH3:21])=[O:19].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:21][O:20][C:18](=[O:19])[C:17]1[CH:22]=[CH:23][CH:24]=[C:15]([CH2:14][N:8]2[CH:7]=[CH:6][C:5]3[C:10](=[N:11][C:2]([Br:1])=[CH:3][CH:4]=3)[C:9]2=[O:12])[CH:16]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 517981Methyl 3-(bromomethyl)benzoateHCID 178517617HCID 178517617, compound

Product 1

HCID 86591200HCID 86591200, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The alkylation of 7-bromo-1-hydroxy-8-azaisoquinoline (1.00 g, 4.46 mmol) using methyl 3-(bromomethyl)benzoate (1.53 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): 3-[1-oxo-7-(3-phenyl-prop-1-ynyl)-1H-8-azaisoquinolin-2-ylmethyl]benzoic acid methyl ester

Workup

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

Sources & evidence

ORD record
ord-f94a272f47f3414d84bcb04e4eb22db5
Source dataset
uspto-grants-2005_12
Patent number
US06977261B2

Reaction notes

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