3-(Trifluoromethyl)aniline → HCID 67237987, compound

HRID 2363131Notes

Reaction equation

HRID 2363131 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]([NH:16][C:17]([C:19]2[N:20]=[C:21](Cl)[O:22][CH:23]=2)=[O:18])[CH3:15])[CH:5]=[C:6]([F:13])[C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10].[F:25][C:26]([F:35])([F:34])[C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][CH:33]=1)[NH2:30].CC([O-])(C)C.[K+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:14]([NH:16][C:17]([C:19]2[N:20]=[C:21]([NH:30][C:29]3[CH:31]=[CH:32][CH:33]=[C:27]([C:26]([F:25])([F:34])[F:35])[CH:28]=3)[O:22][CH:23]=2)=[O:18])[CH3:15])[CH:5]=[C:6]([F:13])[C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10]

Participants

8

Reactant 4

HCID 73753-(Trifluoromethyl)anilineHCID 634876Binap, (A+-)-HCID 23665647Potassium tert-butoxideHCID 671108872-Chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide

Product 1

HCID 67237987HCID 67237987, compoundYield 7.6%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 5 ml glass tube were placed 2-chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide (100 mg, 0.26 mmol), 3-trifluoromethyl aniline (170 mg, 1.05 mmol), t-BuOK (30 mg, 0.26 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (BINAP, 8.1 mg, 0.013 mmol), Pd(OAc)2 (2.9 mg, 0.013 mmol), DMF (1 mL), and a magnetic stir bar. The vial was sealed with septum and placed into the Microwave cavity. The vial was irradiated in a Microwave synthesizer at 130° C. for 4 min. The mixture was diluted with EtOAc and washed with 1N HCl and water. The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The crude residue was purified by column chromatography (gradient 12% to 100% EtOAc in n-hexane) to give title compound (10 mg, 7.5%).

Workup

  1. customIn a 5 ml glass tube were placed
  2. customThe vial was sealed with septum
  3. customThe vial was irradiated in a Microwave synthesizer at 130° C. for 4 min
  4. washwashed with 1N HCl and water
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by column chromatography (gradient 12% to 100% EtOAc in n-hexane)

Sources & evidence

ORD record
ord-e9d3fc3646ea41f0a12cd360000ae4ec
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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