(2s)-Glycidyl indol-4-yl ether → HCID 57101364, compound

HRID 977411Notes

Reaction equation

HRID 977411 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12]3[CH2:13][CH2:14][NH:15][CH2:16][CH:17]=3)=[CH:8][NH:9]2)=[CH:5][CH:4]=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>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12]3[CH2:13][CH2:14][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)[CH2:16][CH:17]=3)=[CH:8][NH:9]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 10943254(2s)-Glycidyl indol-4-yl etherHCID 130190056-methoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Product 1

HCID 57101364HCID 57101364, 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-methoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (0.80 g, 3.5 mmol) and (S)-(+)-4-(oxiranylmethoxy)-1H-indole (0.66 g, 3.5 mmol). The resulting free base was recrystallized from methanol to yield a white crystalline solid. Yield 0.63 g (43%). mp 155°-160° C. FDMS m/e=417 (M+ of free base). α[D]589 =+4.30 (c=0.98, methanol/dimethylsulfoxide).

Workup

  1. customThe resulting free base was recrystallized from methanol
  2. customto yield a white crystalline solid

Sources & evidence

ORD record
ord-2d11550c8285415baf7eb57427a37adb
Source dataset
uspto-grants-1997_03
Patent number
US05614523

Reaction notes

Loading…