3-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indole → HCID 10111423, compound

HRID 1359051Notes

Reaction equation

HRID 1359051 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:26][C:17]3=[C:18]4[C:23](=[CH:24][CH:25]=[C:16]3[O:15][CH2:14]2)[N:22]=[CH:21][CH:20]=[CH:19]4)(=O)=O)=CC=1.[NH:27]1[CH2:32][CH:31]=[C:30]([C:33]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[NH:35][CH:34]=2)[CH2:29][CH2:28]1>CS(C)=O>[NH:35]1[C:36]2[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:33]([C:30]2[CH2:31][CH2:32][N:27]([CH2:12][CH:13]3[O:26][C:17]4=[C:18]5[C:23](=[CH:24][CH:25]=[C:16]4[O:15][CH2:14]3)[N:22]=[CH:21][CH:20]=[CH:19]5)[CH2:28][CH:29]=2)=[CH:34]1

Participants

4

Reactant 2

HCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleHCID 12042423HCID 12042423, compound

Product 1

HCID 10111423HCID 10111423, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
77.5 °C

Procedure

(2R)-2,3-Dihydro[1,4]dioxino[2,3-f]quinolin-2-ylmethyl 4-methylbenzenesulfonate (0.50 g, 1.34 mmole) and 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (0.72 g, 3.65 mmole) were combined in 60 mL of DMSO and heated at 75-80° C. under nitrogen for 6 hours. After cooling to room temperature, the mixture was partitioned between 400 mL each of ethyl acetate and saturated sodium bicarbonate solution. The organic phase was removed, washed with saturated brine, dried over magnesium sulfate and concentrated to an oil in vacuum. This was column chromatographed on silica gel using first ethyl acetate to elute impurities and then 3% methanol in ethyl acetate to elute 0.110 g of the product as a light yellow solid. This was recrystallized from ethanol to give 0.050 g of the (S)-enantiomer of the title compound as a light yellow solid hemihydrate (m.p. 217° C.).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between 400 mL each of ethyl acetate and saturated sodium bicarbonate solution
  3. customThe organic phase was removed
  4. washwashed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to an oil in vacuum
  7. customThis was column chromatographed on silica gel using first ethyl acetate
  8. washto elute impurities
  9. wash3% methanol in ethyl acetate to elute 0.110 g of the product as a light yellow solid
  10. customThis was recrystallized from ethanol

Sources & evidence

ORD record
ord-ba96af3f0b0343338d6323079411c5a4
Source dataset
uspto-grants-2003_07
Patent number
US06599915B2

Reaction notes

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