Potassium Carbonate → HCID 19102608, compound

HRID 1198547Notes

Reaction equation

HRID 1198547 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](/[CH:18]=[CH:19]/[C:20]([O:22][CH3:23])=[O:21])=[C:13]2[C:17]=1[NH:16][CH:15]=[CH:14]2)[C:2]1C=CC=CC=1.BrCC#[N:27].C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)(=O)C.[Pd].C(C(C)=O)C>[C:2]([CH2:1][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[C:13]2[C:17]=1[NH:16][CH:15]=[CH:14]2)#[N:27]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 19102568HCID 19102568, compound

Product 1

HCID 19102608HCID 19102608, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 7-benzyloxy-4-(2(E)-methoxycarbonylethenyl)indole (0.50 g, 1.63 mmol) in methanol (40 ml) and ethyl acetate (10 ml) was hydrogenated at 60 p.s.i. over 10% palladium on charcoal (0.10 g) for 3 hours. The catalyst was filtered off and the filtrate was evaporated. A stirred solution of the residue and bromoacetonitrile (0.12 ml, 1.72 mmol) in methyl ethyl ketone was heated under reflux with solid anhydrous potassium carbonate (0.48 g, 3.4 mmol) for 3.5 hours, poured onto ice-hydrochloric acid and extracted with dichloromethane. The extract was dried and evaporated and the residue was chromatographed on silica in ethyl acetate-hexane (1:3) to give a pale solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. additionpoured onto ice-hydrochloric acid
  4. extractionextracted with dichloromethane
  5. customThe extract was dried
  6. customevaporated
  7. customthe residue was chromatographed on silica in ethyl acetate-hexane (1:3)
  8. customto give a pale solid

Sources & evidence

ORD record
ord-c8e1f92f0bf64a739bcbbd959323d076
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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