5-Iodo-2-methoxy-3-methylpyridine → 1-(3-Chloro-benzyl)-3-(6-methoxy-5-methyl-pyridine-3-carbonyl)-1H-quinolin-4-one

HRID 227083Notes

Reaction equation

HRID 227083 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].I[C:27]1[CH:28]=[C:29]([CH3:35])[C:30]([O:33][CH3:34])=[N:31][CH:32]=1.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:27]2[CH:32]=[N:31][C:30]([O:33][CH3:34])=[C:29]([CH3:35])[CH:28]=2)=[O:5])=[CH:7]1

Participants

5

Reactant 3

HCID 534159905-Iodo-2-methoxy-3-methylpyridineHCID 577546151-(3-Chloro-benzyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amideHCID 178418918HCID 178418918, compound

Product 1

HCID 577545001-(3-Chloro-benzyl)-3-(6-methoxy-5-methyl-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 119 mg (0.33 mmol) of 1-(3-chloro-benzyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide in 1 mL THF and 183 mg (0.73 mmol) of 5-iodo-2-methoxy-3-methyl-pyridine in 1 mL THF with 0.38 mL 2M isopropylmagnesium chloride. Yield: 86 mg of a white powder. LC-MSD, m/z for C24H19ClN2O3 [M+H]+=419.1, 421.1; HPLC retention time: 3.1 min.

Sources & evidence

ORD record
ord-364169cc1817497484717ffe0066f792
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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