Potassium Carbonate → HCID 10295642, compound

HRID 1267872Notes

Reaction equation

HRID 1267872 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+].[F:33][C:34]1[CH:35]=[C:36]2[C:40](=[CH:41][CH:42]=1)[NH:39][CH:38]=[C:37]2[C:43]1[CH2:44][CH2:45][NH:46][CH2:47][CH:48]=1>O1CCCC1.CN(C)C=O>[F:33][C:34]1[CH:35]=[C:36]2[C:40](=[CH:41][CH:42]=1)[NH:39][CH:38]=[C:37]2[C:43]1[CH2:44][CH2:45][N:46]([CH2:12][CH: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)[CH2:47][CH:48]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 113449595-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 12051141HCID 12051141, compound

Product 1

HCID 10295642HCID 10295642, 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-ylmethyl 4-methylbenzenesulfonate (0.25 g, 0.66 mmole) and potassium carbonate (0.22 g, 1.55 mmole) in 1:1 tetrahydrofuran/dimethylformamide (20 mL) was added 0.45 g (2.08 mmole) of 5-fluoro-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole. The reaction mixture was refluxed under nitrogen for six hours. After completion, 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 4% methanol/methylene chloride to elute the desired product as an oil, which was crystallized from isopropanol with the addition of a solution of oxalic acid in hot isopropanol to give 0.040 g (6%) of the (S)-enantiomer of the title compound as a dark yellow solid, m.p. 146-148° C.

Workup

  1. temperatureThe reaction mixture was refluxed under nitrogen for six hours
  2. customAfter completion, the mixture was evaporated to dryness under reduced pressure
  3. customchromatographed on silica gel with methylene chloride
  4. customto remove impurities and 4% methanol/methylene chloride
  5. washto elute the desired product 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-be926fec194b490aab9b97620fa4da01
Source dataset
uspto-grants-2003_04
Patent number
US06555560B2

Reaction notes

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