Sodium Bicarbonate → HCID 10177548, compound

HRID 411600Notes

Reaction equation

HRID 411600 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:18][C:17]3[CH:19]=[C:20]([O:23][CH3:24])[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[NH:25]1[CH2:30][CH:29]=[C:28]([C:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[NH:33][CH:32]=2)[CH2:27][CH2:26]1.C(=O)(O)[O-].[Na+]>CN(C)C=O.O1CCCC1>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:16]2[O:15][CH2:14][CH:13]([CH2:12][N:25]3[CH2:26][CH:27]=[C:28]([C:31]4[C:39]5[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=5)[NH:33][CH:32]=4)[CH2:29][CH2:30]3)[O:18][C:17]=2[CH:19]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleHCID 11792132HCID 11792132, compound

Product 1

HCID 10177548HCID 10177548, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

[(2R)-7-Methoxy-2,3-dihydro-benzo[1,4]dioxin-2-yl]methyl 4-methylbenzenesulfonate (1.5 g, 4.3 mmole) was dissolved in a mixture of dimethylformamide/tetrahydrofuran (1:1 v/v, 30 mL) and 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (0.80 g, 4.0 mmole) added, followed by sodium bicarbonate (1.0 g), and the mixture was refluxed under nitrogen for 18 hours. The solvent was removed under vacuum and the residue partitioned between 400 mL each of methylene chloride and water. The layers were separated and the organic phase was washed with water and saturated sodium chloride solution, dried over potassium carbonate and filtered. The filtrate was evaporated to a foam (1.6 g). Chromatography on silica gel using 4% methanol in chloroform as eluant gave 0.20 g of the (S)-enantiomer of the title compound as a yellow solid, m.p. 166-168° C.

Workup

  1. additionadded
  2. temperaturethe mixture was refluxed under nitrogen for 18 hours
  3. customThe solvent was removed under vacuum
  4. customthe residue partitioned between 400 mL each of methylene chloride and water
  5. customThe layers were separated
  6. washthe organic phase was washed with water and saturated sodium chloride solution
  7. dry with materialdried over potassium carbonate
  8. filtrationfiltered
  9. customThe filtrate was evaporated to a foam (1.6 g)

Sources & evidence

ORD record
ord-68bc75c5f44d4b6799b87c78322e1a02
Source dataset
uspto-grants-2003_05
Patent number
US06559169B2

Reaction notes

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