Tetrahydrofuran → 1-(6-Bromo-pyridin-2-ylmethyl)-3-(4-methoxy-3-methyl-benzoyl)-1H-quinolin-4-one

HRID 227031Notes

Reaction equation

HRID 227031 reaction equation
CON(C)[C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[N:19]=2)[CH:7]=1)=[O:5].[CH2:26]1[CH2:30][O:29][CH2:28][CH2:27]1>COC1C=CC([Mg]Br)=CC=1C>[Br:24][C:20]1[N:19]=[C:18]([CH2:17][N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:15](=[O:16])[C:6]([C:4](=[O:5])[C:6]3[CH:15]=[CH:14][C:30]([O:29][CH3:28])=[C:26]([CH3:27])[CH:4]=3)=[CH:7]2)[CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 577545321-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide

Product 1

HCID 577546461-(6-Bromo-pyridin-2-ylmethyl)-3-(4-methoxy-3-methyl-benzoyl)-1H-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 178491913HCID 178491913, compoundSolvent

Procedure

Experimental conditions analogous to those described for Step 6 of Example 60 from 120 mg (0.30 mmol) of 1-(6-bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide in 1 mL THF and 1.3 mL 0.5M 4-methoxy-3-methylphenylmagnesium bromide. Yield: 102 mg of a white solid. LC-MSD, m/z for C24H19BrN2O3 [M+H]+=463.0, 465.0; HPLC retention time: 2.5 min.

Sources & evidence

ORD record
ord-9a5c972ecfe04d3b95ba77a953a83bba
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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