Tri-o-tolylphosphine → HCID 68444846, compound

HRID 227497Notes

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].C([Sn](CCCC)(CCCC)[C:37]1[CH:42]=[N:41][CH:40]=[CH:39][N:38]=1)CCC.[C:51]1(C)C=CC=C[C:52]=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>[N:26]1([S:23]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([C:37]4[CH:42]=[N:41][CH:40]=[CH:39][N:38]=4)[CH:3]=3)[NH:7][C:6]=2[C:20]([O:22][CH2:51][CH3:52])=[O:21])(=[O:24])=[O:25])[CH2:27][CH2:28][O:29][CH2:30][CH2:31]1

Participants

Conditions

Temperature: 120 °C

Procedure

1-tert-Butyl-2-ethyl 5-iodo-3-(morpholin-4-ylsulfonyl)-1H-indole-1,2-dicarboxylate (100 mg, 0.18 mmol, 1.0 equiv), 2-(tributylstannyl)pyrazine (91 mg, 0.25 mmol, 1.4 equiv), tri-o-tolylphosphine (11 mg, 0.04 mmol, 0.2 equiv) and palladium(II)acetate (4.0 mg, 0.02 mmol, 0.1 equiv) were dissolved in 2 mL of dry DMF and heated to 120° C. for 18 hours. 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 (ethyl acetate/dichloromethane) provided the titled compound. Proton NMR for the product was consistent with the titled compound. ESI+MS: 417.4 [M+H]+.

Workup

temperatureThe mixture was cooled to ambient temperature
extractionthe aqueous layer was extracted 3 times with dichloromethane
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by flash chromatography through silica gel (ethyl acetate/dichloromethane)

Sources & evidence

ORD record: ord-c1bc3c1708be4b00b3b95c704bee7d10
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560546B2

Reaction notes

Loading…