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-(5-chloro-thiophene-2-carbonyl)-1H-quinolin-4-one

HRID 227062Notes

Reaction equation

HRID 227062 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].[Cl:26][C:27]1[S:31][C:30]([Mg]Br)=[CH:29][CH:28]=1>C1COCC1>[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:30]3[S:31][C:27]([Cl:26])=[CH:28][CH:29]=3)=[O:5])=[CH:7]2)[CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 577545321-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amideHCID 178478193HCID 178478193, compound

Product 1

HCID 577547331-(6-Bromo-pyridin-2-ylmethyl)-3-(5-chloro-thiophene-2-carbonyl)-1H-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 0.5 mL THF and 2.0 mL 0.25M 5-chloro-2-thienylmagnesium bromide. Yield: 56 mg of a white solid. LC-MSD, m/z for C20H12BrClN2O2S [M+H]+=458.9, 460.9, 462.9; HPLC retention time: 2.5 min.

Sources & evidence

ORD record
ord-4f4d99d845524bd3888cdcde6d17d3c7
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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