Methyl iodide → 1-(4-Fluorophenyl)-5-(2-methyltetrazol-5-yl)-1H-indole

HRID 394584Notes

Reaction equation

HRID 394584 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4[NH:21][N:20]=[N:19][N:18]=4)=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.I[CH3:23]>CN1C(=O)CCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4[N:18]=[N:19][N:20]([CH3:23])[N:21]=4)=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 178505847HCID 178505847, compound

Product 1

HCID 181771991-(4-Fluorophenyl)-5-(2-methyltetrazol-5-yl)-1H-indole

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-5-tetrazol-5-yl-1H-indole (8a) (19 g) in NMP (200 mL) potassium t-butoxide (8.5 g) was added cautiously at 10° C. followed by dropwise addition of iodomethane (22 g) during 20 minutes. The mixture was allowed to reach room temperature and stirred for another 2 hours. Crude title compound was worked up according to the general procedure above. Purification was performed by column chromatography on silica gel using dichloromethane as eluent. Yield 15 g, mp 131-133° C.

Workup

  1. customto reach room temperature

Sources & evidence

ORD record
ord-51be8a46fcde439c90d16105f14bbdab
Source dataset
uspto-grants-2003_08
Patent number
US06602889B1

Reaction notes

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