Potassium Carbonate → 2-Benzyloxy-[1,1';2',1'']terphenyl-4''-sulfonic acid (1-phenyl-methanoyl)-amide

HRID 269543

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[C:16](B(O)O)=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:25]1[CH:30]=[CH:29][C:28]([S:31]([NH:34][C:35]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:36])(=[O:33])=[O:32])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1.C(O)C>C(OCC)(=O)C.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>[C:37]1([C:35]([NH:34][S:31]([C:28]2[CH:29]=[CH:30][C:25]([C:16]3[C:15]([C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:26][CH:27]=2)(=[O:33])=[O:32])=[O:36])[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2′-benzyloxy-biphenyl-2-boronic acid (100 mg, 0.33 mmol), 4-bromo-N-(1-phenyl-methanoyl)-benzenesulfonamide (95 mg, 0.28 mmol), potassium carbonate (309 mg, 2.24 mmol), and tetrakis(triphenylphosphine)palladium(0) (38 mg, 0.033 mmol) in 1:1 toluene/ethanol (5 ml) was stirred and heated at 90° C. under nitrogen for 16 hours. After cooling the mixture was diluted with ethyl acetate and water. The organic phase was dried and evaporated. The residue was chromatographed eluting with ethyl acetate/iso-hexane (1:4-1:1) to give the title compound as a colourless solid. (40 mg 23%).

Workup

temperatureAfter cooling the mixture
customThe organic phase was dried
customevaporated
customThe residue was chromatographed
washeluting with ethyl acetate/iso-hexane (1:4-1:1)

Sources & evidence

ORD record: ord-f223f0c3235c49968b831589534a2cf9
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446222B2

Linked notes

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