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

HRID 227047Notes

Reaction equation

HRID 227047 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=C([Mg]Br)C=CC=1OC>[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:26]3[CH:27]=[CH:26][C:30]([O:29][CH3:28])=[C:28]([O:29][CH3:30])[CH:27]=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 577546581-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethoxy-benzoyl)-1H-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 178491916HCID 178491916, compoundSolvent

Procedure

Experimental conditions analogous to those described for Step 6 of Example 60 from 90 mg (0.22 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 0.98 mL 0.5M 3,4-dimethoxyphenylmagnesium bromide. Yield: 55 mg of a white solid. LC-MSD, m/z for C24H19BrN2O4 [M+H]+=479.0, 481.0; HPLC retention time: 2.1 min.

Sources & evidence

ORD record
ord-5f8c6892a03241a79410e761749d5843
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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