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-fluoro-4-methoxy-benzoyl)-1H-quinolin-4-one

HRID 227051Notes

Reaction equation

HRID 227051 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].[F:26][C:27]1[CH:28]=[C:29]([Mg]Br)[CH:30]=[CH:31][C:32]=1[O:33][CH3:34]>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](=[O:5])[C:29]3[CH:30]=[CH:31][C:32]([O:33][CH3:34])=[C:27]([F:26])[CH:28]=3)=[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 178491915HCID 178491915, compound

Product 1

HCID 577546131-(6-Bromo-pyridin-2-ylmethyl)-3-(3-fluoro-4-methoxy-benzoyl)-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 1 mL THF and 0.98 mL 0.5M 3-fluoro-4-methoxyphenylmagnesium bromide. Yield: 57 mg of a white solid. 1H NMR (400 MHz, CDCl3): δ 4.0 (s, 3H), 5.5 (s, 2H), 6.9-7.0 (m, 2H), 7.3-7.4 (m, 1H), 7.4-7.6 (m, 3H), 7.6-7.7 (m, 3H), 8.3 (s, 1H), 8.4-8.5 (m, 1H). LC-MSD, m/z for C23H16BrFN2O3 [M+H]+=467.0, 469.0; HPLC retention time: 2.3 min.

Sources & evidence

ORD record
ord-13526f46df1244a2877327d10167ab81
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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