Cesium carbonate → HCID 86591199, compound

HRID 489180Notes

Reaction equation

HRID 489180 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:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:22][O:21][C:19](=[O:20])[C:18]1[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][CH:17]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 178517617HCID 178517617, compound

Product 1

HCID 86591199HCID 86591199, 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 4-(bromomethyl)benzoate (1.53 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). The solid is crystallized from hexanes/ethyl acetate 2:1, the white crystals collected by filtration and dried to give the desired product. Step (2): 4-[1-oxo-7-(3-phenyl-prop-1-ynyl)-1H-8-azaisoquinolin-2-ylmethyl]benzoic acid methyl ester

Workup

  1. customThe solid is crystallized from hexanes/ethyl acetate 2:1
  2. filtrationthe white crystals collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-4aa908dc0cf94deca45ec8f23e7c4b2e
Source dataset
uspto-grants-2005_12
Patent number
US06977261B2

Reaction notes

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