Potassium Carbonate → HCID 9887363, compound

HRID 496046Notes

Reaction equation

HRID 496046 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:26][O:25][C:16]3[CH:17]=[CH:18][C:19]4[CH2:20][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:33]1[CH2:38][CH:37]=[C:36]([C:39]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[NH:41][CH:40]=2)[CH2:35][CH2:34]1>O1CCCC1.CN(C)C=O>[O:14]1[C:15]2[C:24]3[O:23][CH2:22][CH2:21][CH2:20][C:19]=3[CH:18]=[CH:17][C:16]=2[O:25][CH2:26][CH:13]1[CH2:12][N:33]1[CH2:34][CH:35]=[C:36]([C:39]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[NH:41][CH:40]=2)[CH2:37][CH2:38]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleHCID 12051141HCID 12051141, compound

Product 1

HCID 9887363HCID 9887363, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a mixture of (2R)-2,3,8,9-tetrahydro-7H-[1,4]dioxino[2,3-h]chromen-2-yl-methyl 4-methylbenzenesulfonate (0.30 g, 0.80 mmole) and potassium carbonate (0.22 g, 1.55 mmole) in 1:1 tetrahydrofuran/dimethylformamide (20 mL) was added 0.47 g (2.38 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 as an as an oil, which was crystallized from isopropanol with the addition of a solution of oxalic acid in hot isopropanol to give 0.070 g (6%) of the (S)-enantiomer of the title compound as an orange solid, m.p. 140° 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 as an as an oil, which
  6. customwas crystallized from isopropanol with the addition of a solution of oxalic acid in hot isopropanol

Sources & evidence

ORD record
ord-09c94ba5b54e45a4af4411df802cfd47
Source dataset
uspto-grants-2005_09
Patent number
US06943178B2

Reaction notes

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