1-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide → HCID 57754699, compound

HRID 227066Notes

Reaction equation

HRID 227066 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[CH:32]=[CH:31][C:30]([Mg]Br)=[CH:29][C:28]=1[O:35][CH3:36]>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:30]3[CH:31]=[CH:32][C:27]([Cl:26])=[C:28]([O:35][CH3:36])[CH:29]=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 178492973HCID 178492973, compound

Product 1

HCID 57754699HCID 57754699, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Experimental conditions analogous to those described for Step 6 of Example 60 from 92 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 2.01 mL 0.25M 4-chloro-3-methoxyphenylmagnesium bromide. Yield: 40 mg of a white solid. LC-MSD, m/z for C23H16BrClN2O3 [M+H]+=483.0, 485.0; HPLC retention time: 2.5 min.

Sources & evidence

ORD record
ord-11a889bfb37048158108f292ae510040
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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