2-Fluorophenylboronic acid → N-[5-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-5-(2-fluorophenyl)-2-thiophenesulfonamide

HRID 130458Notes

Reaction equation

Br[C:2]1[S:6][C:5]([S:7]([NH:10][C:11]2[CH:16]=[C:15]([N:17]3[CH2:22][C@H:21]([CH3:23])[NH:20][C@H:19]([CH3:24])[CH2:18]3)[CH:14]=[CH:13][C:12]=2[O:25][CH3:26])(=[O:9])=[O:8])=[CH:4][CH:3]=1.[F:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1B(O)O.CC(C)([O-])C.[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>[CH3:24][C@H:19]1[NH:20][C@@H:21]([CH3:23])[CH2:22][N:17]([C:15]2[CH:14]=[CH:13][C:12]([O:25][CH3:26])=[C:11]([NH:10][S:7]([C:5]3[S:6][C:2]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[F:27])=[CH:3][CH:4]=3)(=[O:9])=[O:8])[CH:16]=2)[CH2:18]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 5-bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-2-thiophenesulfonamide (E122) (150 mg, 0.33 mmol) and (2-fluorophenyl)boronic acid (91 mg, 0.65 mmol) in DME (3 ml) was added potassium tert-butoxide (329 mg, 2.94 mmol) and tetrakis(triphenylphosphine)palladium(0) (37 mg, 0.033 mmol) in water (1 ml) and the resulting mixture stirred in a microwave (set at high absorbance) at 100° C. for 30 minutes. The resulting mixture was then reduced in vacuo, azeotroped with toluene (×3) and purified using SCX then mass directed autoprep HPLC to afford the title product (E124). MS (ES+) m/e 476 [M+H]+.

Workup

customazeotroped with toluene (×3)
custompurified

Sources & evidence

ORD record: ord-361d8583b945418d8f4049300501e87e
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07381728B2

Reaction notes

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