Sodium Methoxide → 1-(3-Chloro-benzyl)-3-(6-methoxy-pyridine-3-carbonyl)-1H-quinolin-4-one

HRID 227086Notes

Reaction equation

HRID 227086 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[C:8]([C:17]([C:19]2[CH:20]=[N:21][C:22](Cl)=[CH:23][CH:24]=2)=[O:18])=[CH:7]1.[CH3:29][O-:30].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[C:8]([C:17]([C:19]2[CH:20]=[N:21][C:22]([O:30][CH3:29])=[CH:23][CH:24]=2)=[O:18])=[CH:7]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 577546041-(3-Chloro-benzyl)-3-(6-chloro-pyridine-3-carbonyl)-1H-quinolin-4-one

Product 1

HCID 577546421-(3-Chloro-benzyl)-3-(6-methoxy-pyridine-3-carbonyl)-1H-quinolin-4-oneYield 89.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Experimental conditions analogous to those described for Step 6 of Example 60, from 151 mg (0.37 mmol) of 1-(3-chloro-benzyl)-3-(6-chloro-pyridine-3-carbonyl)-1H-quinolin-4-one and 170 mg (3.15 mmol) of sodium methoxide were stirred in 2 mL of dry methanol in a sealed vessel at 75° C. for 2 h. The reaction mixture was evaporated and purified by flash chromatography to give 134 mg of a white powder. LC-MSD, m/z for C23H17ClN2O3 [M+H]+=405.1, 407.1; HPLC retention time: 2.3 min.

Workup

  1. customThe reaction mixture was evaporated
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-b3dd80b3e27b48c489ebeebe36ec1ce6
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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