Sodium Bicarbonate → HCID 10177548, compound

HRID 1823842Notes

Reaction equation

HRID 1823842 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-b7f47aae8c4c409ebfb86b86b2661051
Source dataset
uspto-grants-2006_05
Patent number
US07041683B2

Reaction notes

Loading…