Oxalic Acid → 2-[4-(6-Chloro-3-indolyl)-1,2,3,6-tetra-hydropyridin-1-yl]-1-(4-indolyloxy)ethane ethanedioate

HRID 481643Notes

Reaction equation

HRID 481643 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[C:6]2[CH:7]=[CH:8][NH:9][C:10]=2[CH:11]=[CH:12][CH:13]=1.[Cl:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19]([C:24]3[CH2:25][CH2:26][NH:27][CH2:28][CH:29]=3)=[CH:20][NH:21]2)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38]>CN(C)C=O.C(OCC)C>[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38].[Cl:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19]([C:24]3[CH2:25][CH2:26][N:27]([CH2:2][CH2:3][O:4][C:5]4[CH:13]=[CH:12][CH:11]=[C:10]5[C:6]=4[CH:7]=[CH:8][NH:9]5)[CH2:28][CH:29]=3)=[CH:20][NH:21]2)=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 11430Potassium CarbonateHCID 100598546-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 106317214-(2-chloroethoxy)-1H-indole

Product 1

HCID 867500062-[4-(6-Chloro-3-indolyl)-1,2,3,6-tetra-hydropyridin-1-yl]-1-(4-indolyloxy)ethane ethanedioate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared in a fashion similar to that described in Example 99 using 1-chloro-2-(1H-indole-4-oxy)ethane (0.359 g, 1.85 mmol) and 6-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (0.500 g, 2.13 mmol) in the presence of 2.0 equivalents of potassium carbonate (0.51 g, 3.7 mmol) in dimethylformamide at 90° C. Yield 0.101 g (14%) of a tan foam. The oxalate salt was prepared by treating the free base with 1.0 equivalent of oxalic acid in diethyl ether and evaporating. mp 120°-124° C. (browns) FDMS m/e=391 (M+ of free base).

Workup

  1. customevaporating

Sources & evidence

ORD record
ord-a3d0be6b8b42479f82de80aabd7b0ef2
Source dataset
uspto-grants-1998_08
Patent number
US05789402

Reaction notes

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