Cesium carbonate → HCID 57809736, compound

HRID 2106024Notes

Reaction equation

HRID 2106024 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([CH3:29])([CH3:28])[CH2:9][C:10]([OH:27])([C:23]([F:26])([F:25])[F:24])[CH2:11][N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[CH:14]=[CH:13]2)[CH:5]=[CH:6][CH:7]=1.[CH3:30][C:31]1[C:35](B(O)O)=[C:34]([CH3:39])[O:33][N:32]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.O.C(O)C>[CH3:30][C:31]1[C:35]([C:2]2[CH:3]=[C:4]([C:8]([CH3:28])([CH3:29])[CH2:9][C:10]([OH:27])([C:23]([F:24])([F:25])[F:26])[CH2:11][N:12]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15](=[O:22])[CH:14]=[CH:13]3)[CH:5]=[CH:6][CH:7]=2)=[C:34]([CH3:39])[O:33][N:32]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 57810005HCID 57810005, compound

Product 1

HCID 57809736HCID 57809736, compound

Reagents, catalysts & solvents 1

HCID 86587095Dimethoxyethane ethanol waterSolvent

Procedure

A mixture of 1-[4-(3-bromophenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1-H-quinolin-4-one (30 mg, 0.064 mmol), 3,5-dimethylisoxazole-4-boronic acid (9 mg, 0.064 mmol, 1 equiv.), bisdichlorotriphenylphosphinopalladium (II) (catalytic amount) and cesium carbonate (21 mg, 0.064 mmol) in 1.1 mL of ethylene glycol dimethyl ether-water-ethanol (7:3:2) was degassed, sealed in a vial, and irradiated twice (microwave) at 160° C. for 300 seconds. The reaction was cooled to room temperature and filtered through CELITE® filter aid. The filtrate was diluted with water and extracted with diethyl ether. The combined organic layers were washed with brine and dried with sodium sulfate. Removal of the volatiles in vacuo provided a residue which was purified by HPLC to give 1-{4-[3-(3,5-dimethylisoxazol-4-yl)phenyl]-2-hydroxy-4-methyl-2-trifluoromethylpentyl}-1H-quinolin-4-one.

Workup

  1. customwas degassed
  2. customsealed in a vial, and
  3. customirradiated twice (microwave) at 160° C. for 300 seconds
  4. filtrationfiltered through CELITE®
  5. filtrationfilter aid
  6. additionThe filtrate was diluted with water
  7. extractionextracted with diethyl ether
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried with sodium sulfate
  10. customRemoval of the volatiles in vacuo
  11. customprovided a residue which
  12. customwas purified by HPLC

Sources & evidence

ORD record
ord-5ebbb4bad136463aaa9a2f5bb5f3bd3b
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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