Methyl iodide → HCID 86690640, compound

HRID 1505605Notes

Reaction equation

[CH:1](NC(C)C)(C)C.[Li].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]([CH2:28][C:29]([F:32])([F:31])[F:30])[S:18]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:20])=[O:19])=[C:12]([F:33])[CH:11]=1.IC>O1CCCC1>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]([CH2:28][C:29]([F:30])([F:31])[F:32])[S:18]([CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:1])(=[O:20])=[O:19])=[C:12]([F:33])[CH:11]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of lithium diisopropylamine (2.0 M in THF/heptane/ethylbenzene) (1.2 mL, 2.5 mmol) at −78° C. was slowly added a solution of N-[(4-bromo-2-fluoro-phenyl)methyl]-1-phenyl-N-(2,2,2-trifluoroethyl)methanesulfonamide (1 g, 2.3 mmol) in tetrahydrofuran (11 mL) and the reaction was stirred at −78° C. for 1 hour. Iodomethane (0.16 mL, 2.5 mmol) was then added and the reaction was warmed to ambient temperature and stirred for 2 hours. The reaction was quenched with saturated aqueous NH4Cl and diluted with EtOAc, washed with 1 N aqueous HCl, and brine, dried with MgSO4, concentrated and purified by silica gel column chromatography (0-30% EtOAc in heptane) to give N-[(4-bromo-2-fluoro-phenyl)methyl]-1-phenyl-N-(2,2,2-trifluoroethyl)ethanesulfonamide (614 mg, 60% yield). LCMS (m/z) ES+ 471 [M+18]+.

Workup

temperaturethe reaction was warmed to ambient temperature
stirringstirred for 2 hours
customThe reaction was quenched with saturated aqueous NH4Cl
additiondiluted with EtOAc
washwashed with 1 N aqueous HCl, and brine
dry with materialdried with MgSO4
concentrationconcentrated
custompurified by silica gel column chromatography (0-30% EtOAc in heptane)

Sources & evidence

ORD record: ord-bcf2ed5e20d0409fa31948c4081c71ee
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216988B2

Reaction notes

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