(2s)-Glycidyl indol-4-yl ether → HCID 57133432, compound

HRID 1901024Notes

Reaction equation

HRID 1901024 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([C:6]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[O:18]1[CH2:20][C@H:19]1[CH2:21][O:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:24]=1[CH:25]=[CH:26][NH:27]2>CO.CS(C)=O>[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([C:6]([CH:12]3[CH2:17][CH2:16][N:15]([CH2:20][C@H:19]([OH:18])[CH2:21][O:22][C:23]4[CH:31]=[CH:30][CH:29]=[C:28]5[C:24]=4[CH:25]=[CH:26][NH:27]5)[CH2:14][CH2:13]3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10943254(2s)-Glycidyl indol-4-yl etherHCID 21268353HCID 21268353, compound

Product 1

HCID 57133432HCID 57133432, compound

Reagents, catalysts & solvents 1

HCID 22036561Dimethyl sulfoxide methanolSolvent

Procedure

The title compound was prepared in a fashion similar to that described in Example 193 from 6,7-dichloro-3-(piperidin-4-yl)-1H-indole (0.80 g, 3.0 mmol) and (S)-(+)-4-(oxiranylmethoxy)-1H-indole (0.58 g, 3.1 mmol). The product was isolated as a white solid. Yield 0.64 g (47%). mp 192°-197° C. FDMS m/e=457 (M+ of free base). α[D]589 =+6.46 (c=0.99, methanol/dimethylsulfoxide).

Workup

  1. customThe product was isolated as a white solid

Sources & evidence

ORD record
ord-4d449f464c2647668eca7d8208f2f2ed
Source dataset
uspto-grants-1996_11
Patent number
US05576321

Reaction notes

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