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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2360164Generated: October 30, 2026

Methyl iodide → HCID 86659885, compound

https://huagongshe.com/reaction/2360164

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantSodium hydrideHCID 24758—
ReactantHCID 86659884HCID 86659884—
SolventDiethyl EtherHCID 3283—
SolventDimethylformamideHCID 6228—
ProductHCID 86659885HCID 8665988567.2%

Reaction Steps

To a solution of 3-(di-n-propylaminocarbonylmethyl)-5-methoxyindole (180 mg, 0.62 mmol) in 1.8 mL of N,N-dimethylformamide was added sodium hydride (55%, 40 mg, 0.93 mmol) at 0° C. After the reaction mixture was stirred at the same temperature for 30 min, methyl iodide (0.10 mL, 1.2 mmol) was added with additional stirring at room temperature for 12 h. After the reaction mixture was diluted with diethyl ether, and washed with water and brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20) to obtain the title compound (126 mg, 67%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08686024B2
Source datasetuspto-grants-2014_04
ORD IDord-d92132542bca43089f2581f8e0f8f4f3
Source noteuspto-grants-2014_04