Potassium Carbonate → HCID 10158852, compound

HRID 1071859Notes

Reaction equation

HRID 1071859 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:27][O:26][C:16]3[CH:17]=[CH:18][C:19]4[C:20](=[O:25])[CH2:21][CH2:22][O:23][C:24]=4[C:15]=3[O:14]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].[NH:34]1[CH2:39][CH:38]=[C:37]([C:40]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[NH:42][CH:41]=2)[CH2:36][CH2:35]1>O1CCCC1.CN(C)C=O>[NH:42]1[C:43]2[C:48](=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:40]([C:37]2[CH2:38][CH2:39][N:34]([CH2:12][CH:13]3[O:14][C:15]4[C:16](=[CH:17][CH:18]=[C:19]5[C:24]=4[O:23][CH2:22][CH2:21][C:20]5=[O:25])[O:26][CH2:27]3)[CH2:35][CH:36]=2)=[CH:41]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleHCID 11188448HCID 11188448, compound

Product 1

HCID 10158852HCID 10158852, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a mixture of [(2R)-7-oxo-2,3,8,9-tetrahydro-7H-[1,4]dioxino[2,3-h]-chromen-2-yl]methyl 4-methylbenzenesulfonate (0.60 g, 1.54 mmole) and potassium carbonate (0.22 g, 1.55 mmole) in 1:1 tetrahydrofuran/dimethyl-formamide (20 mL) was added 0.91 g (4.61 mmole) of 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole. The reaction mixture was refluxed under nitrogen for 6 hours. After the reaction was complete, the mixture was evaporated to dryness under reduced pressure and the residue was column chromatographed on silica gel with methylene chloride to remove impurities and with 3% methanol/methylene chloride to elute the desired product. Evaporation of the product-containing fractions in vacuum gave 0.12 g (18%) of the (S)-enantiomer of the title compound as an off-white solid, m.p. 210° C.

Workup

  1. temperatureThe reaction mixture was refluxed under nitrogen for 6 hours
  2. customthe mixture was evaporated to dryness under reduced pressure
  3. customchromatographed on silica gel with methylene chloride
  4. customto remove impurities
  5. washwith 3% methanol/methylene chloride to elute the desired product
  6. customEvaporation of the product-containing fractions in vacuum

Sources & evidence

ORD record
ord-1c74a7d21b334b86becf88f5c4fed8d8
Source dataset
uspto-grants-2005_06
Patent number
US06906206B2

Reaction notes

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