Ethanol → HCID 57187766, compound

HRID 1779640Notes

Reaction equation

HRID 1779640 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2.[CH3:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:24]=1[NH:23][CH:22]=[C:21]2[C:25]1[CH2:26][CH2:27][NH:28][CH2:29][CH:30]=1.C(O)C>CS(C)=O>[CH3:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:24]=1[NH:23][CH:22]=[C:21]2[C:25]1[CH2:26][CH2:27][N:28]([CH2:3][C@H:2]([OH:1])[CH2:4][O:5][C:6]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:7]=2[CH:8]=[CH:9][NH:10]3)[CH2:29][CH:30]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 10943254(2s)-Glycidyl indol-4-yl etherHCID 11310393HCID 11310393, compound

Product 1

HCID 57187766HCID 57187766, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared in a fashion similar to that described in Example 1 using (S)-(+)-4-(oxiranylmethoxy)-1H-indole (0.389 g, 2.05 mmol) and 7-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (0.400 g, 1.87 mmol) using ethanol as reaction solvent. Yield 0.292 g (39%) as an orange foam. mp 155°-158° C. FDMS m/e=401 (M+ of free base). α[D]589 =+5.9 (c=1.05, dimethylsulfoxide).

Workup

  1. customas reaction solvent

Sources & evidence

ORD record
ord-f15f318df4a44ba0b79706cabbbdbb8b
Source dataset
uspto-grants-1997_05
Patent number
US05627196

Reaction notes

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