Potassium Carbonate → HCID 9910014, compound

HRID 275715Notes

Reaction equation

HRID 275715 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[C:17]([N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]([CH2:29][CH2:30]S(C)(=O)=O)[CH2:21]1)(=[O:19])[CH3:18].C([O-])([O-])=O.[K+].[K+]>CC(CC(C)C)=O>[C:17]([N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]([CH2:29][CH2:30][N:14]2[CH2:13][CH:12]=[C:11]([C:6]3[C:5]4[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=4)[NH:8][CH:7]=3)[CH2:16][CH2:15]2)[CH2:21]1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 100598546-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 18545886HCID 18545886, compound

Product 1

HCID 9910014HCID 9910014, compoundYield 10.4%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of of 6-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (1.6 g), 19a (2.0 g), K2CO3 (4.0 g), and methylisobutylketone (20 ml) was refluxed for 16 hours. The mixture was filtered and evaporated in vacuo, and the residue was purified on silica gel eluted with ethyl acetate-methanol-triethylamine (90:5:5). Crystallization from ethanol gave the title product (0.3 g).

Workup

  1. temperaturewas refluxed for 16 hours
  2. filtrationThe mixture was filtered
  3. customevaporated in vacuo
  4. customthe residue was purified on silica gel
  5. washeluted with ethyl acetate-methanol-triethylamine (90:5:5)
  6. customCrystallization from ethanol

Sources & evidence

ORD record
ord-b811231cbf1a4a6c88805486449770a2
Source dataset
uspto-grants-2002_03
Patent number
US06352988B2

Reaction notes

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