Sodium Carbonate → HCID 57750956, compound

HRID 2283291Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=3)[CH:17]=2)(=[O:15])=[O:14])=[C:6]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:7]=1.[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.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>[Cl:29][C:24]1[CH:23]=[C:22]([C:18]2[CH:17]=[C:16]([S:13]([NH:12][C:5]3[CH:4]=[CH:3][C:2]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:7][C:6]=3[S:8]([NH2:11])(=[O:10])=[O:9])(=[O:15])=[O:14])[CH:21]=[CH:20][CH:19]=2)[CH:27]=[CH:26][C:25]=1[Cl:28]

Participants

Conditions

Temperature: 80 °C

Procedure

5-Bromo-2-[[3-(3,4-dichlorophenyl)phenyl]sulfonylamino]benzenesulfonamide (70 mg, 0.13 mmol) was dissolved in DMF (700 μl), then phenylboronic acid (20 mg, 0.16 mmol) was added followed by the addition of 2M sodium carbonate solution (260 μl). The mixture was subjected to vacuum/argon (×3), tetrakis(triphenylphosphine)palladium (8 mg, 0.05 mol %) was added and the reaction was allowed to stir at 80° C. overnight. The cooled reaction mixture was filtered and was then purified by preparative HPLC (XTerra MS C8 column, acetonitrile/ammonium acetate buffer) to give the title compound (23 mg, 32%).

Workup

additionwas added
customThe cooled reaction mixture
filtrationwas filtered
customwas then purified by preparative HPLC (XTerra MS C8 column, acetonitrile/ammonium acetate buffer)

Sources & evidence

ORD record: ord-96ca22eb2ab640a896eda9a4e75d7720
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145380B2

Reaction notes

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