1-(6-Methyl-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl amide → 3-(6-Ethyl-pyridine-3-carbonyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one
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]([CH3:24])[N: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>[CH2:26]([C:28]1[N:29]=[CH:30][C:31]([C:4]([C:6]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[N:19]=3)[CH:7]=2)=[O:5])=[CH:32][CH:33]=1)[CH3:27]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Experimental conditions analogous to those described for Step 6 of Example 60, from 85 mg (0.25 mmol) of 1-(6-methyl-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide in 2.5 mL THF and 129 mg (0.56 mmol) of 2-ethyl-5-iodo-pyridine in 1 mL THF with 0.29 mL 2M isopropylmagnesium chloride. Yield: 41 mg of a white powder. LC-MSD, m/z for C24H21N3O2 [M+H]+=384.1; HPLC retention time: 0.7 min.
Sources & evidence
- ORD record
- ord-e49016b1ecc340ac917690d43ef8aedc
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07557213B2
Reaction notes
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