Dimethylformamide → 1-(4-Chlorobenzyl)-3-(2-(3-pyridyl)ethenyl)-5-(2-quinolylmethoxy)indole

HRID 486060Notes

Reaction equation

HRID 486060 reaction equation
[H-].[Na+].[Cl-].[N:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:5]=1.CN(C)C=O.[Cl:35][C:36]1[CH:65]=[CH:64][C:39]([CH2:40][N:41]2[C:49]3[C:44](=[CH:45][C:46]([O:50][CH2:51][C:52]4[CH:61]=[CH:60][C:59]5[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=5)[N:53]=4)=[CH:47][CH:48]=3)[C:43]([CH:62]=O)=[CH:42]2)=[CH:38][CH:37]=1>O.C(OCC)(=O)C>[Cl:35][C:36]1[CH:37]=[CH:38][C:39]([CH2:40][N:41]2[C:49]3[C:44](=[CH:45][C:46]([O:50][CH2:51][C:52]4[CH:61]=[CH:60][C:59]5[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=5)[N:53]=4)=[CH:47][CH:48]=3)[C:43]([CH:62]=[CH:10][C:6]3[CH:5]=[N:4][CH:9]=[CH:8][CH:7]=3)=[CH:42]2)=[CH:64][CH:65]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 19097338HCID 19097338, compoundHCID 22325077Triphenyl(3-pyridylmethyl)phosphonium chloride

Product 1

HCID 545011021-(4-Chlorobenzyl)-3-(2-(3-pyridyl)ethenyl)-5-(2-quinolylmethoxy)indoleYield 30.5%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

A suspension of sodium hydride (60%-oil suspension, 0.39 g), 3-picolyl-triphenylphosphonium chloride (2.55 g) and N,N-dimethylformamide was stirred for 20 minutes, followed by the addition of 1-(4-chlorobenzyl)-3-formyl-5-(2-quinolylmethoxy)indole (3.0 g). The mixture was stirred for an additional 10 hours and then poured into water-ethyl acetate (50% v/v). The organic layer was separated, washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The resultant crude product was purified by chromatography on silica gel using 50%-ethyl acetate in n-hexanes as eluent to yield 1-(4-chlorobenzyl)-3-(2-(3-pyridyl)ethenyl)-5-(2-quinolylmethoxy)indole (1.0 g), m.p. 169°-171° C.

Workup

  1. stirringThe mixture was stirred for an additional 10 hours
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resultant crude product was purified by chromatography on silica gel using 50%-ethyl acetate in n-hexanes as eluent

Sources & evidence

ORD record
ord-6430d7dc8c0b4b4dba5c96136a706f3d
Source dataset
uspto-grants-1994_03
Patent number
US05290788

Reaction notes

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