1-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide → 1-(6-Bromo-pyridin-2-ylmethyl)-3-(3-methyl-pyridine-2-carbonyl)-1H-quinolin-4-one

HRID 227053Notes

Reaction equation

HRID 227053 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]>C1COCC1.CC1C([Mg]Br)=NC=CC=1>[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]([C:7]3[C:6]([CH3:4])=[CH:15][CH:14]=[CH:9][N:8]=3)=[O:5])=[CH:7]2)[CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 1

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

Product 1

HCID 577547071-(6-Bromo-pyridin-2-ylmethyl)-3-(3-methyl-pyridine-2-carbonyl)-1H-quinolin-4-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 178426302HCID 178426302, 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 1.96 mL 0.25M 3-methyl-2-pyridylmagnesium bromide. Yield: 22 mg of a white solid. LC-MSD, m/z for C22H16BrN3O2 [M+H]+=434.0, 436.0; HPLC retention time: 1.8 min.

Sources & evidence

ORD record
ord-27539c1542084c819d460e5f2580c43b
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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