Cesium carbonate → HCID 117601319, compound

HRID 1773710Notes

Reaction equation

HRID 1773710 reaction equation
Br[C:2]1[CH:13]=[CH:12][C:5]([NH:6][CH2:7][C:8]([F:11])([F:10])[F:9])=[C:4]([Cl:14])[CH:3]=1.[CH3:15][C:16]1[C:20](B(O)O)=[C:19]([CH3:24])[O:18][N:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.O>[Cl:14][C:4]1[CH:3]=[C:2]([C:20]2[C:16]([CH3:15])=[N:17][O:18][C:19]=2[CH3:24])[CH:13]=[CH:12][C:5]=1[NH:6][CH2:7][C:8]([F:11])([F:10])[F:9]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 43347377HCID 43347377, compound

Product 1

HCID 117601319HCID 117601319, compound

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-Bromo-2-chloro-N-(2,2,2-trifluoroethyl)aniline (5280 mg, 18.3 mmol), 3,5-dimethylisoxazole-4-boronic acid, pinacol ester (4082.76 mg, 18.3 mmol), PEPPSI″-IPr catalyst (1247.24 mg, 1.83 mmol), Cesium carbonate (17889.52 mg, 54.91 mmol) in 120 mL DME:H2O (2:1) was heated to 90° C. under argon. The reaction mixture was then cooled and partitioned between water and ethyl acetate. The organic layer was washed with water then brine and dried over sodium sulfate. Purification on silica gel (Hexanes/EtOAc) afforded 2-chloro-4-(3,5-dimethylisoxazol-4-yl)-N-(2,2,2-trifluoroethyl)aniline.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. custompartitioned between water and ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialbrine and dried over sodium sulfate
  5. customPurification on silica gel (Hexanes/EtOAc)

Sources & evidence

ORD record
ord-8caf49ba605a4759a85f078ebcd3c2e0
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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