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

HRID 227072Notes

Reaction equation

HRID 227072 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]([CH3:24])[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>[CH3:28][O:29][C:30]1[CH:14]=[CH:15][C:6]([C:4]([C:6]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[N:19]=3)[CH:7]=2)=[O:5])=[CH:4][C:26]=1[CH3:27]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 577545121-(6-Methyl-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl amide

Product 1

HCID 577547363-(4-Methoxy-3-methyl-benzoyl)-1-(6-methyl-pyridin-2-ylmethyl)-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 168 mg (0.50 mmol) of 1-(6-methyl-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide in 2.5 mL THF and 2.5 mL 0.5M 4-methoxy-3-methylphenylmagnesium bromide. Yield: 107 mg of a white solid. LC-MSD, m/z for C25H22N2O3 [M+H]+=399.1; HPLC retention time: 2.1 min.

Sources & evidence

ORD record
ord-1712324be3d14d2fb7f36205f5eb2a2f
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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