Methyl iodide → 4-(Benzyloxy)-1-methyl-1H-indole

HRID 490811Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18]I.[H-].[Na+]>>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 24758Sodium hydride

HCID 884654-(phenylmethoxy)-1H-indole

Product 1

HCID 247769014-(Benzyloxy)-1-methyl-1H-indole

Procedure

Compounds of Formula I can be prepared as illustrated by exemplary reaction in Scheme 1. Reaction of 4-benzyloxy-indole with MeI in the presence of a base such as NaH produced 4-benzyloxy-1-methyl-indole. The benzyl protecting group was removed by hydrogenation to give the 4-hydroxy-1-methyl-indole. Reaction of 4-hydroxy-1-methyl-indole with an aryl-aldehyde such as 5-bromoveratraldehyde and malononitrile in the presence of a base such as piperidine produced the substituted 7-methyl-pyrrolo[2,3-h]chromene.

Workup

customCompounds of Formula I can be prepared
customas illustrated by exemplary reaction in Scheme 1

Sources & evidence

ORD record: ord-df73c1e276a34e649959f5acc7ef1727
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528164B2

Reaction notes

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