Potassium Phosphate, Tribasic → HCID 67309479, compound
Reaction equation
[CH:1]1(B(O)O)[CH2:3][CH2:2]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:35]1[CH:39]=[CH:38][N:37]([S:40]([C:43]2[CH:48]=[CH:47][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:45][CH:44]=2)(=[O:42])=[O:41])[CH:36]=1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:1]1([C:39]2[CH:35]=[CH:36][N:37]([S:40]([C:43]3[CH:44]=[CH:45][C:46]([C:49]([F:51])([F:52])[F:50])=[CH:47][CH:48]=3)(=[O:41])=[O:42])[CH:38]=2)[CH2:3][CH2:2]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
Cyclopropyl boronic acid (1.6 g, 18.7 mmol), palladium (II) acetate (323 mg, 1.44 mmol), tricyclohexylphosphine (808 mg, 2.88 mmol) and potassium phosphate (10.7 g, 50.5 mmol) were added to a solution of 3-bromo-1-(4-(trifluoromethyl)phenylsulfonyl)-1H-pyrrole (5.11 g, 14.4 mmol) in toluene/H2O (75 mL, 19/1). The resulting suspension was evacuated and purged with nitrogen three times and then placed in an oil bath pre-heated to 100° C. The reaction was stirred for 6 h and was subsequently concentrated under vacuum. The residue was purified on a silica gel column (eluant hexane/EtOAc, 9/1, v/v) to give compound 113 (3.21 g, 10.1 mmol, 71%). MS (ESI) 316.1 (M+H).
Workup
- customThe resulting suspension was evacuated
- custompurged with nitrogen three times
- customplaced in an oil bath
- concentrationwas subsequently concentrated under vacuum
- customThe residue was purified on a silica gel column (eluant hexane/EtOAc, 9/1
Sources & evidence
- ORD record
- ord-97e1dbe4ca4b485bb4c316f4f99a3738
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08283358B2
Reaction notes
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