Potassium Carbonate → HCID 10929467, compound

HRID 1741847Notes

Reaction equation

HRID 1741847 reaction equation
[OH:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([C:8]2[CH:9]=[C:10]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:11]3[C:16]=2[CH:15]=[CH:14][CH:13]=[CH:12]3)=[O:7])=[CH:4][CH:3]=1.Br[CH:28]([C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH:38]([CH3:40])[CH3:39])=[CH:33][CH:32]=1)[CH2:29][CH3:30].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:37]([C:34]1[CH:33]=[CH:32][C:31]([CH:28]([O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([C:8]3[CH:9]=[C:10]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:11]4[C:16]=3[CH:15]=[CH:14][CH:13]=[CH:12]4)=[O:7])=[CH:25][CH:26]=2)[CH2:29][CH3:30])=[CH:36][CH:35]=1)[CH:38]([CH3:40])[CH3:39]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10956141Benzene, 1-(1-bromopropyl)-4-(2-methylpropyl)-HCID 11824313Ethyl 4-[1-(4-hydroxybenzoyl)indolizin-3-yl]butyrate

Product 1

HCID 10929467HCID 10929467, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 4-[1-(4-hydroxybenzoyl)indolizin-3-yl]butyrate (61 mg), 1-bromo-1-(4-isobutylphenyl)propane (53 mg) and potassium carbonate (72 mg) in N,N-dimethylformamide (2 ml) was stirred at room temperature for 18 hours. The reaction mixture was filtered and the filtrate was poured into a mixture of ethyl acetate and 0.5N hydrochloric acid. The organic layer was separated, washed with water and brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel eluting with n-hexane and ethyl acetate (2:1) to give ethyl 4-[1-[4-[1-(4-isobutylphenyl)propyloxy]benzoyl]indolizin-3-yl]butyrate (80 mg) as an oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate was poured into a mixture of ethyl acetate and 0.5N hydrochloric acid
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel eluting with n-hexane and ethyl acetate (2:1)

Sources & evidence

ORD record
ord-a80def6471c14d74aa6f4c5d7e62c1d6
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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