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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1051490Generated: October 25, 2026

Methyl iodide → 6-Bromo-1,3-dimethyl-1H-indole

https://huagongshe.com/reaction/1051490

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantSodium hydrideHCID 24758—
Reactant6-Bromo-3-methyl-1H-indoleHCID 53402958—
SolventDimethylformamideHCID 6228—
Product6-Bromo-1,3-dimethyl-1H-indoleHCID 23383511—

Reaction Steps

To a solution of 6-bromo-3-methyl-1H-indole (200 mg, 0.95 mmol) in DMF (8 mL) was added NaH (114 mg, 2.85 mmol, m %/60%). The mixture was stirred at room temperature for 1 h before the addition of MeI (162 mg, 1.14 mmol). The system was stirred at room temperature for 4 h then the mixture was quenched with water and extracted with EtOAc. The organic layer was concentrated to give crude product which was used in next step without further purification. LCMS (m/z): 224.1 [M+H]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09388173B2
Source datasetuspto-grants-2016_07
ORD IDord-bd6104608632445aabcb26bc882c55c3
Source noteuspto-grants-2016_07