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

HRID 227046Notes

Reaction equation

HRID 227046 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].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>[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]([C:32]3[CH:27]=[CH:28][CH:29]=[C:30]([C:33]([F:36])([F:35])[F:34])[N:31]=3)=[O:5])=[CH:7]2)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 455981185-Iodo-2-(trifluoromethyl)pyridineHCID 577545321-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amideHCID 178418918HCID 178418918, compound

Product 1

HCID 577546261-(6-Bromo-pyridin-2-ylmethyl)-3-(6-trifluoromethyl-pyridine-2-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 (0.30 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 239 mg (0.66 mmol) of 75% 5-iodo-2-trifluoromethyl-pyridine in 1 mL THF with 0.37 mL 2M isopropylmagnesium chloride. Yield: 78 mg of a white powder. LC-MSD, m/z for C22H13BrF3N3O2 [M+H]+=488.0, 490.0; HPLC retention time: 2.4 min.

Sources & evidence

ORD record
ord-7a3c467093a647d88ab37e04c122dec0
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

Loading…