(2s)-Glycidyl indol-4-yl ether → HCID 56985622, compound

HRID 1901028Notes

Reaction equation

HRID 1901028 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=3)=[CH:7][NH:8]2)=[CH:4][C:3]=1[O:17][CH3:18].[O:19]1[CH2:21][C@H:20]1[CH2:22][O:23][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:25]=1[CH:26]=[CH:27][NH:28]2>CS(C)=O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH2:12][CH2:13][N:14]([CH2:21][C@H:20]([OH:19])[CH2:22][O:23][C:24]4[CH:32]=[CH:31][CH:30]=[C:29]5[C:25]=4[CH:26]=[CH:27][NH:28]5)[CH2:15][CH:16]=3)=[CH:7][NH:8]2)=[CH:4][C:3]=1[O:17][CH3:18]

Participants

4

Reactant 2

HCID 10943254(2s)-Glycidyl indol-4-yl etherHCID 21268275HCID 21268275, compound

Product 1

HCID 56985622HCID 56985622, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared in a fashion similar to that described in Example 193 from 6-chloro-5-methoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (0.80 g, 3.0 mmol) and (S)-(+)-4-(oxiranylmethoxy)-1H-indole (0.60 g, 3.2 mmol). The product was isolated as a yellow foam. Yield 260 mg (19%). mp 115°-120° C. FDMS m/e=452 (M+ of free base). α[D]589 =+6.62 (c=1.03, dimethylsulfoxide).

Workup

  1. customThe product was isolated as a yellow foam

Sources & evidence

ORD record
ord-35625b5963ea41989b9b8ddda43add3c
Source dataset
uspto-grants-1996_11
Patent number
US05576321

Reaction notes

Loading…