1-(3-Chloro-benzyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide → 1-(3-Chloro-benzyl)-3-(6-ethyl-pyridine-3-carbonyl)-1H-quinolin-4-one

HRID 227085Notes

Reaction equation

HRID 227085 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]([Cl:24])[CH:19]=2)[CH:7]=1)=[O:5].[CH2:26]([C:28]1[CH:33]=[CH:32][C:31](I)=[CH:30][N:29]=1)[CH3:27].C([Mg]Cl)(C)C>C1COCC1>[Cl:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[CH2:17][N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:15](=[O:16])[C:6]([C:4]([C:31]2[CH:30]=[N:29][C:28]([CH2:26][CH3:27])=[CH:33][CH:32]=2)=[O:5])=[CH:7]1

Participants

5

Reactant 3

HCID 577546151-(3-Chloro-benzyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amideHCID 668794762-Ethyl-5-iodo-pyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 577547401-(3-Chloro-benzyl)-3-(6-ethyl-pyridine-3-carbonyl)-1H-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Experimental conditions analogous to those described for Step 6 of Example 60, from 300 mg (0.84 mmol) of 1-(3-chloro-benzyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide in 2 mL THF and 433 mg (1.86 mmol) of 2-ethyl-5-iodo-pyridine in 2 mL THF with 0.97 mL 2M isopropylmagnesium chloride. Yield: 127 mg of a white powder. LC-MSD, m/z for C24H19ClN2O2 [M+H]+=403.1, 405.1; HPLC retention time: 1.8 min.

Sources & evidence

ORD record
ord-a67aab3e3a6d4ed0b81f84bee12f435b
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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