Cesium fluoride → HCID 68444896, compound

HRID 227498Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](C(OCCC(C)(C)C)=O)[C:6]([C:20]([O-:22])=[O:21])=[C:5]2[S:23]([N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)(=[O:25])=[O:24].[O:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[CH:34]=[C:33]1B(O)O.[C:44](P(C(C)(C)C)C(C)(C)C)(C)(C)[CH3:45].[F-].[Cs+].C([O-])(O)=O.[Na+]>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[CH:34]=[C:33]1[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:20]([O:22][CH2:44][CH3:45])=[O:21])=[C:5]2[S:23]([N:26]1[CH2:27][CH2:28][O:29][CH2:30][CH2:31]1)(=[O:24])=[O:25]

Participants

Conditions

Temperature: 90 °C

Procedure

1-tert-Butyl-2-ethyl 5-iodo-3-(morpholin-4-ylsulfonyl)-1H-indole-1,2-dicarboxylate (54 mg, 0.096 mmol, 1.0 equiv), 1-benzofuran-2-ylboronic acid (22 mg, 0.13 mmol, 1.4 equiv), tri-t-butylphosphine (3.9 mg, 0.02 mmol, 0.2 equiv) and palladium(II)acetate (2.1 mg, 0.01 mmol, 0.1 equiv) and cesium fluoride (73 mg, 0.48 mmol, 5.0 equiv) were dissolved in 5 mL of dry DME and heated to 90° C. for 3 hours. The mixture was cooled to ambient temperature, poured into aqueous saturated NaHCO3 and the aqueous layer was extracted 3 times with ethyl acetate. The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to provide the titled compound. ESI+MS: 455.1 [M+H]+.

Workup

temperatureThe mixture was cooled to ambient temperature
extractionthe aqueous layer was extracted 3 times with ethyl acetate
dry with materialThe combined organic extracts were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e707f78623754aefae9024e3a1d3195f
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560546B2

Reaction notes

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