Potassium Carbonate → 1-(4-Cyano-2-methoxybenzyl)-6-nitroindole

HRID 358741Notes

Reaction equation

[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=1[O:23][CH3:24].C(=O)([O-])[O-].[K+].[K+]>>[C:19]([C:18]1[CH:21]=[CH:22][C:15]([CH2:14][N:10]2[C:11]3[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=3)[CH:8]=[CH:9]2)=[C:16]([O:23][CH3:24])[CH:17]=1)#[N:20]

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 785026-Nitro-1H-indole

HCID 147529954-(Bromomethyl)-3-methoxybenzonitrile

Product 1

HCID 147529961-(4-Cyano-2-methoxybenzyl)-6-nitroindoleYield 78%

Procedure

6-Nitroindole was alkylated with 4-bromomethyl-3-methoxybenzonitrile in the presence of potassium carbonate using the general procedure described in Ex 1(a) to give 1-(4-cyano-2-methoxybenzyl)-6-nitroindole (W) in 78% yield as a solid, m.p. 190.5°-191° C. (b) The nitrile W was converted to the corresponding tetrazole, 1-(2-methoxy-4-[1-(H)-tetrazol-5-yl]benzyl)6-nitroindole (X), obtained in 86% yield as a yellow-green solid, m.p. 258°-260° C. (d) using the general procedure of Example 67.

Sources & evidence

ORD record: ord-f2c3bf03828b48aab968043c8686e8e5
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04997844

Reaction notes

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