Ethanol → 2-(2-Chloro-phenyl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid (4'-acetylamino-biphenyl-4-yl)-amide

HRID 1673000Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].Br[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]2[N:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[N:27]=[C:26]([C:36]([F:39])([F:38])[F:37])[CH:25]=2)=[O:23])=[CH:17][CH:16]=1.C(O)C>CS(C)=O.CC(O)=O.CC(O)=O.C1CCC([N-]C2CCCCC2)CC1.C1CCC([N-]C2CCCCC2)CC1.[Pd+2]>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:22]([C:24]3[N:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[Cl:35])[N:27]=[C:26]([C:36]([F:37])([F:38])[F:39])[CH:25]=3)=[O:23])=[CH:19][CH:20]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

In a 4 ml vial was added 22.3 mg (0.125 mmol) of (4-acetylaminophenyl)boronic acid, 11 mg (0.025 mmol) of N-(4-bromophenyl)-1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide, 200 μL of a saturated CsCO3 solution of ethanol and 10 μg of DAPCy. The vial was sealed and heated to 60° C. overnight. The crude product was dissolved up in 200 μL of DMSO and injected directly on a reverse phase LCMS preparative instrument. The relevant fraction was collected dried to afford 2-(2-Chloro-phenyl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid (4′-acetylamino-biphenyl-4-yl)-amide (4.3 mg, 0.0086 mmol: 34% yield as an off white solid. MS (ESI) m/z 499 [M+H]+.

Workup

customThe vial was sealed
customThe relevant fraction was collected
customdried

Sources & evidence

ORD record: ord-44b8abc9a74c48eeb2a45a336cbf5587
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998995B2

Reaction notes

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