Potassium Carbonate → HCID 10273998, compound

HRID 1359058Notes

Reaction equation

HRID 1359058 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:28][C:17]3=[C:18]4[C:23](=[CH:24][CH:25]=[C:16]3[O:15][CH2:14]2)[N:22]=[C:21]([CH2:26][CH3:27])[CH:20]=[CH:19]4)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].[NH:35]1[CH2:40][CH:39]=[C:38]([C:41]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[NH:43][CH:42]=2)[CH2:37][CH2:36]1>C1COCC1.CN(C=O)C>[CH2:26]([C:21]1[CH:20]=[CH:19][C:18]2[C:23](=[CH:24][CH:25]=[C:16]3[O:15][CH2:14][CH:13]([CH2:12][N:35]4[CH2:36][CH:37]=[C:38]([C:41]5[C:49]6[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=6)[NH:43][CH:42]=5)[CH2:39][CH2:40]4)[O:28][C:17]3=2)[N:22]=1)[CH3:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleHCID 12042436HCID 12042436, compound

Product 1

HCID 10273998HCID 10273998, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a solution of (2R)-8-ethyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-ylmethyl 4-methylbenzenesulfonate (0.60 g, 1.5 mmole) and potassium carbonate (0.65 g, 4.70 mmole) in 30 mL of 1:1 THF/DMF was added 0.90 g (4.5 mmole) of 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole. The mixture was heated at reflux under nitrogen for 6 hours. After cooling to room temperature, the mixture was concentrated to dryness under vacuum and the residue column chromatographed on silica gel using first methylene chloride to elute impurities and then 3% methanol in methylene chloride to elute the product. The product-containing fractions were concentrated in vacuum and the residue recrystallized from ethanol to give 0.42 g of the (S)-enantiomer of the title compound as a yellow solid (m.p. 190° C.).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux under nitrogen for 6 hours
  3. concentrationthe mixture was concentrated to dryness under vacuum
  4. customthe residue column chromatographed on silica gel using first methylene chloride
  5. washto elute impurities
  6. wash3% methanol in methylene chloride to elute the product
  7. concentrationThe product-containing fractions were concentrated in vacuum
  8. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-c5b2d376ffc24037978b06c602f76c4d
Source dataset
uspto-grants-2003_07
Patent number
US06599915B2

Reaction notes

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