Reaction #314249

ord-da831cdc68454e4c84cab66ce1472532

Reaction equation

CON(C)C(=O)c1cn(Cc2cccc(Br)n2)c2ccccc2c1=O
1-(6-bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide
Clc1cc[c]([Mg][Br])cc1
4-chlorophenylmagnesium bromide
→
O=C(c1ccc(Cl)cc1)c1cn(Cc2cccc(Br)n2)c2ccccc2c1=O
1-(6-Bromo-pyridin-2-ylmethyl)-3-(4-chloro-benzoyl)-1H-quinolin-4-one

Reactants

CON(C)C(=O)c1cn(Cc2cccc(Br)n2)c2ccccc2c1=O
1-(6-bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide
—
white solid
Clc1cc[c]([Mg][Br])cc1
4-chlorophenylmagnesium bromide

Reagents

None

Solvents

C1CCOC1
THF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Experimental conditions analogous to those described for Step 6 of Example 60 from 150 mg (0.37 mmol) of 1-(6-bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide in 3 mL THF and 0.82 mL 1M 4-chlorophenylmagnesium bromide. Yield: 73 mg of a white solid. LC-MSD, m/z for C22H14BrClN2O2 [M+H]+=453.0, 455.0; HPLC retention time: 2.6 min.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07557213B2uspto-grants-2009_07