3-(Chloromethyl)pyridine → HCID 18926590, compound

HRID 1600172Notes

Reaction equation

HRID 1600172 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.C[Mg]Br.Cl[CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)=[CH:5][NH:6]2

Participants

5

Reactant 3

HCID 183583-(Chloromethyl)pyridineHCID 6764944-BromoindoleHCID 178418573HCID 178418573, compound

Product 1

HCID 18926590HCID 18926590, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treatment of 4-bromo-1H-indole (J.Org.Chem., 48 2066(1983)) (16.95 g) with methyl magnesium bromide (34.6 ml of 3M solution in ether) followed by a dichloromethane solution of 3-(chloromethyl)pyridine (prepared from 17.02 g of 3-(chloromethyl)pyridine hydrochloride) according to the method of Preparation 6 gave the title compound (7.80 g), m.p. 173°-174° C. Found: C,58.90; H,3.88; N,9.80. C,14 H11BrN2 requires: C,58.55; H,3.86; N,9.76%.

Workup

  1. customaccording to the method of Preparation 6

Sources & evidence

ORD record
ord-cec935570c614e03a4280969fa7349ff
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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