Potassium Carbonate → HCID 67121204, compound

HRID 1510454Notes

Reaction equation

HRID 1510454 reaction equation
B1(C=C)OB([CH:7]=[CH2:8])OB(C=C)O1.C1C=CN=CC=1.Br[C:20]1[C:21]([C:35]([NH:37][CH:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)=[O:36])=[N:22][O:23][C:24]=1[C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:38]1([NH:37][C:35]([C:21]2[C:20]([CH:7]=[CH2:8])=[C:24]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)[O:23][N:22]=2)=[O:36])[CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27348062,4,6-Trivinylboroxin-Pyridine ComplexHCID 25181909HCID 25181909, compound

Product 1

HCID 67121204HCID 67121204, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

Tetrakis(triphenylphosphine)palladium (0) (57.9 mg, 0.05 mmol) was added to a stirred suspension of 2,4,6-trivinylcyclotriboroxane pyridine complex (121 mg, 0.50 mmol), 4-bromo-N-cyclopentyl-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxamide (202 mg, 0.50 mmol) and potassium carbonate (138 mg, 1.0 mmol) in DME (4.7 mL) and water (1.6 mL) and heated to 100° C. for 2 hours. The reaction mixture was allowed to cool to room temperature and partitioned between water and ethylacetate. The organics were dried over magnesium sulphate and concentrated in vacuo. Purification by silica gel chromatography eluting with heptane to 20% ethylacetate in heptane to obtain N-cyclopentyl-5-(4-(trifluoromethyl)phenyl)-4-vinylisoxazole-3-carboxamide (140 mg, 0.40 mmol).

Workup

  1. temperatureto cool to room temperature
  2. custompartitioned between water and ethylacetate
  3. dry with materialThe organics were dried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel chromatography
  6. washeluting with heptane to 20% ethylacetate in heptane

Sources & evidence

ORD record
ord-0496efd28ccd42c9a3806ce2a99f9add
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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