Tri-o-tolylphosphine → HCID 10339432, compound

HRID 227485Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH2:13])=[O:12])=[C:5]2[S:14]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)(=[O:16])=[O:15].C([Sn](CCCC)(CCCC)[C:28]1[O:29][CH:30]=[CH:31][CH:32]=1)CCC.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C([O-])(O)=O.[Na+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:29]1[CH:30]=[CH:31][CH:32]=[C:28]1[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH2:13])=[O:12])=[C:5]2[S:14]([N:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1)(=[O:16])=[O:15]

Participants

Conditions

Temperature: 90 °C

Procedure

5-Bromo-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxamide (50 mg, 0.13 mmol, 1.0 equiv), 2-(tributylstannyl)furan (48 μL, 0.15 mmol, 1.2 equiv), tri-o-tolylphosphine (7.8 mg, 0.03 mmol, 0.2 equiv) and palladium(II)acetate (2.9 mg, 0.015 mmol, 0.1 equiv) were dissolved in 5 mL of dry DMF and heated to 90° C. for 1 hour. The mixture was cooled to ambient temperature, poured into aqueous saturated NaHCO3 and the aqueous layer was extracted 3 times with dichloromethane. The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash chromatography through silica gel (0-5% MeOH with 10% NH4OH/dichloromethane) provided the titled compound. Proton NMR for the product was consistent with the titled compound. ESI+MS: 376.1 [M+H]+.

Workup

temperatureThe mixture was cooled to ambient temperature
extractionthe aqueous layer was extracted 3 times with dichloromethane
dry with materialThe combined organic extracts were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by flash chromatography through silica gel (0-5% MeOH with 10% NH4OH/dichloromethane)

Sources & evidence

ORD record: ord-7ddee3b6948d422babb71003582baef2
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560546B2

Reaction notes

Loading…