Ethanol → HCID 57325182, compound

HRID 1900994Notes

Reaction equation

HRID 1900994 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:24]=[C:23]2[C:19]([C:20]([C:25]3[CH2:26][CH2:27][NH:28][CH2:29][CH:30]=3)=[CH:21][NH:22]2)=[CH:18][CH:17]=1.C(O)C>CS(C)=O>[CH3:15][C:16]1[CH:24]=[C:23]2[C:19]([C:20]([C:25]3[CH2:26][CH2:27][N:28]([CH2:3][C@H:2]([OH:1])[CH2:4][O:5][C:6]4[CH:14]=[CH:13][CH:12]=[C:11]5[C:7]=4[CH:8]=[CH:9][NH:10]5)[CH2:29][CH:30]=3)=[CH:21][NH:22]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 104207266-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 10943254(2s)-Glycidyl indol-4-yl ether

Product 1

HCID 57325182HCID 57325182, 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 6-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (0.400 g, 1.87 mmol) using ethanol as reaction solvent. Yield 0.260 g (35%) as an orange foam. mp 99°-103° C. (dec). FDMS m/e=401 (M+ of free base). α[D]589 =+5.1 (c=0.98, dimethylsulfoxide).

Workup

  1. customas reaction solvent

Sources & evidence

ORD record
ord-ba72dc283e3d4d048158c0df7de35c68
Source dataset
uspto-grants-1996_11
Patent number
US05576321

Reaction notes

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