Ethylene → HCID 10065524, compound

HRID 227488Notes

Reaction equation

HRID 227488 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:23]1(C)C=CC=C[C:24]=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.C=C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:17]1([S:14]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([CH:23]=[CH2:24])[CH:3]=3)[NH:7][C:6]=2[C:11]([NH2:13])=[O:12])(=[O:16])=[O:15])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 6325EthyleneHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 10023126HCID 10023126, compound

Product 1

HCID 10065524HCID 10065524, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5-Bromo-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxamide (106 mg, 0.273 mmol, 1.0 equiv), palladium(II)acetate (12 mg, 0.012 mmol, 0.1 equiv), tri-o-tolylphosphine (31 mg, 0.10 mmol, 0.2 equiv) and triethylamine (150 μL, 1.03 mmol, 2.0 equiv) were dissolved in 5 mL of DMF, the vessel was charged with 1 atm of ethylene and heated to 100° C. for 24 hours. The title compound was obtained after purification by preparative reversed phase HPLC. Proton NMR for the product was consistent with the titled compound. HRMS (ES) exact mass calculated for C15H18N3O4S (M+H+): 336.1013. Found 336.1016.

Sources & evidence

ORD record
ord-471a7d38258b4ae1b678995945abca7a
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

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