Potassium Carbonate → 3-[4-(6-Trifluoromethyl-3-indolyl)-1,2,3,6-tetrahydropyridin-1-yl]-1-(4-indolyloxy)propane

HRID 565547Notes

Reaction equation

HRID 565547 reaction equation
[F:1][C:2]([F:19])([F:18])[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.Cl[CH2:21][CH2:22][CH2:23][O:24][C:25]1[C:26]2[CH:27]=[CH:28][NH:29][C:30]=2[CH:31]=[CH:32][CH:33]=1.C(=O)([O-])[O-].[K+].[K+]>>[F:19][C:2]([F:1])([F:18])[C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12]3[CH2:13][CH2:14][N:15]([CH2:21][CH2:22][CH2:23][O:24][C:25]4[CH:33]=[CH:32][CH:31]=[C:30]5[C:26]=4[CH:27]=[CH:28][NH:29]5)[CH2:16][CH:17]=3)=[CH:8][NH:9]2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 112425616-trifluoromethyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 116941694-(3-chloropropoxy)-1H-indole

Product 1

HCID 212682863-[4-(6-Trifluoromethyl-3-indolyl)-1,2,3,6-tetrahydropyridin-1-yl]-1-(4-indolyloxy)propane

Procedure

The title compound was prepared in a fashion similar to that described in Example 192 from 6-trifluoromethyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (0.50 g, 1.9 mmol), 1-chloro-3-(1H-indole-4-oxy)propane (0.39 g, 1.9 mmol) and potassium carbonate (0.29 g, 2.1 mmol). The product was isolated as a white foam. Yield 0.53 g (64%). mp 190-195° C. FDMS m/e=440 (M+ of free base).

Workup

  1. customThe product was isolated as a white foam

Sources & evidence

ORD record
ord-aa107dfb1fbf498396bb77a2e55cc814
Source dataset
uspto-grants-2001_01
Patent number
US06172073B2

Reaction notes

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