Triethylamine → HCID 68680510, compound

HRID 1820551Notes

Reaction equation

HRID 1820551 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[NH:7][C:6]([C:12]([N:14]1[CH2:19][CH2:18][C:17]([F:21])([F:20])[CH2:16][CH2:15]1)=[O:13])=[CH:5]2.C(N(CC)CC)C.[C:29]([O:32][CH2:33]C)(=[O:31])C>C(O)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:33][O:32][C:29]([C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[NH:7][C:6]([C:12]([N:14]1[CH2:19][CH2:18][C:17]([F:21])([F:20])[CH2:16][CH2:15]1)=[O:13])=[CH:5]2)=[O:31]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 68681937HCID 68681937, compound

Product 1

HCID 68680510HCID 68680510, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolvent

Procedure

The mixture consistent of 100 mg (0.265 mmol) (5-bromo-7-chloro-1H-indol-2-yl)-(4,4-difluoro-piperidin-1-yl)-methanone, 15 mg (0.0184 mmol) 1,1′-bis(diphenylphosphino)ferrocene palladium dichloride and 55.6 μL (0.398 mmol) triethylamine in 1 mL ethanol and 1 mL ethyl acetate was stirred overnight at 100° C. under an atmosphere of carbon monoxide (120 bar). After cooling to room temperature the reaction mixture is filtered, evaporated and chromatographed on silica gel with ethyl acetate:n-heptane (1:2 v/v) as eluant to give the desired compound as a colorless solid (69%).

Workup

  1. filtrationis filtered
  2. customevaporated
  3. customchromatographed on silica gel with ethyl acetate:n-heptane (1:2 v/v) as eluant

Sources & evidence

ORD record
ord-8edfa84a4a4643d08eb5126512545422
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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