5-Iodo-2-(trifluoromethyl)pyridine → 1-(6-Methyl-pyridin-2-ylmethyl)-3-(6-trifluoromethyl-pyridine-3-carbonyl)-1H-quinolin-4-one

HRID 227075Notes

Reaction equation

HRID 227075 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].I[C:27]1[CH:28]=[CH:29][C:30]([C:33]([F:36])([F:35])[F:34])=[N:31][CH:32]=1.C([Mg]Cl)(C)C>C1COCC1>[CH3:24][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]([C:27]3[CH:32]=[N:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)=[O:5])=[CH:7]2)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 455981185-Iodo-2-(trifluoromethyl)pyridineHCID 577545121-(6-Methyl-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl amideHCID 178418918HCID 178418918, compound

Product 1

HCID 577546251-(6-Methyl-pyridin-2-ylmethyl)-3-(6-trifluoromethyl-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 120 mg (0.36 mmol) of 1-(6-methyl-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide in 1 mL THF and 214 mg (0.78 mmol) of 5-iodo-2-trifluoromethyl-pyridine in 1.5 mL THF with 0.41 mL 2M isopropylmagnesium chloride. Yield: 81 mg of a white powder. LC-MSD, m/z for C23H16F3N3O2 [M+H]+=424.1; HPLC retention time: 2.2 min.

Sources & evidence

ORD record
ord-e1cc9c2edd3546c3ace89953ab20f2bb
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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