HCID 86598745, compound → HCID 11292243, compound

HRID 2104487Notes

Reaction equation

HRID 2104487 reaction equation
CON(C)[C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[C:22]([F:25])([F:24])[F:23])=[O:5].[CH3:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[Mg]Br>C1COCC1>[CH3:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[C:22]([F:25])([F:23])[F:24])=[O:5]

Participants

4

Reactant 2

HCID 86598745HCID 86598745, compoundHCID 178424303HCID 178424303, compound

Product 1

HCID 11292243HCID 11292243, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Methoxy-N-methyl-4-phenyl-8-(trifluoromethyl)quinoline-3-carboxamide (0.100 g, 0.278 mmol) was taken into THF (3 mL) and cooled to 0° C. where 2-methylphenylmagnesium bromide was added. The reaction was then allowed to stir at room temperature overnight. The reaction was quenched with MeOH and 2 M HCl and stirred for 5 minutes. The organics were removed and the resulting aqueous layer was extracted with methylene chloride, dried and concentrated. Column chromatography using 10% ethyl acetate in hexane afforded 0.057 g of the desired product as a white solid. MS (ESI) m/z 392 ([M+H]+); Anal. Calcd. for C24H16F3NO: C, 73.65; H, 4.12; N, 3.58. Found: C, 73.88; H, 3.87; N, 3.29.

Workup

  1. additionwas added
  2. customThe reaction was quenched with MeOH and 2 M HCl
  3. stirringstirred for 5 minutes
  4. customThe organics were removed
  5. extractionthe resulting aqueous layer was extracted with methylene chloride
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-35cbb620a87045b5be618aa9343a3618
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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