Potassium Carbonate → HCID 22563203, compound

HRID 982690Notes

Reaction equation

HRID 982690 reaction equation
[Br-].[C:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:18])[CH2:11][N+:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)#[N:3].C(=O)([O-])[O-].[K+].[K+].[CH3:25][C:26](=[O:29])[C:27]#[CH:28]>O1CCCC1>[C:26]([C:27]1[CH:28]=[C:11]([C:10](=[O:18])[C:7]2[CH:6]=[CH:5][C:4]([C:2]#[N:3])=[CH:9][CH:8]=2)[N:12]2[C:17]=1[CH:16]=[CH:15][CH:14]=[CH:13]2)(=[O:29])[CH3:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15018Butyn-2-oneHCID 22563201HCID 22563201, compound

Product 1

HCID 22563203HCID 22563203, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A slurry of 1-(2-(4-cyano-phenyl)-2-oxo-ethyl)-pyridinium bromide (11) (4.04 grams, 13.2 mmol) and potassium carbonate (2.21 grams, 16.0 mmol) in tetrahydrofuran (250 mL) was stirred at room temperature for 10 minutes. To it was added 3-butyn-2-one (1.4 mL, 16.0 mmol), and the reaction mixture was kept stirring at room temperature for 6 hours. The insoluble material was filtered off and the filtrate was concentrated in vacuo. The residue was subjected to column chromatographic purification on silica gel using 3:1 hexane and ethyl acetate (Rf 0.2) to afford 1-acetyl-3-(4-cyanobenzoyl)indolizine (12) as a yellow solid (2.55 grams, 72%). 1H NMR (CDCl3) δ 2.56 (s, 3H), 7.23 (m, 1H), 7.62 (m, 2H), 7.90 (m, 4H), 8.72 (d, J=9.0, 1H), 10.02 (d, J=6.6, 1H); ESMS calcd (C18H12N2O2): 288.1. found: 289.1 (M+H)+.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was subjected to column chromatographic purification on silica gel using 3:1 hexane and ethyl acetate (Rf 0.2)

Sources & evidence

ORD record
ord-f871d691268a46368ae67baea691c9b6
Source dataset
uspto-grants-2005_03
Patent number
US06861436B2

Reaction notes

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