1-Bromo-2-methylpropane → HCID 86722206, compound

HRID 623365Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[CH2:23][CH:24]([CH3:26])[CH3:25].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:19])[F:20])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-bromo-N-(2-trifluoromethyl-phenyl)-benzenesulfonamide (710 mg, 1.87 mmol), 1-bromo-2-methyl propane (305 μL, 2.80 mmol) and K2CO3 (412 mg, 2.99 mmol) in DMF (5 mL) was heated at 90° C. for 18 hours. The cooled mixture was diluted with EtOAc, washed with water (3×) and brine, dried over Na2SO4 and concentrated under vacuum. Purification by silica gel column chromatography (0-15% EtOAc in cyclohexane) and triturating with pentane gave 4-bromo-N-isobutyl-N-(2-trifluoromethyl-phenyl)-benzenesulfonamide (562 mg, 69% yield) as a colourless crystalline solid. 1H NMR (300 MHz, CDCl3) δ 7.76-7.71 (m, 1H), 7.72-7.55 (m, 2H), 7.57-7.56 (m, 2H), 7.58-7.43 (m, 2H), 7.13-7.09 (m, 1H), 3.53-3.08 (m, 2H), 1.66-1.63 (m, 1H), 0.90 (d, J=6.5 Hz, 3H), 0.81 (d, J=6.7 Hz, 3H), LCMS (m/z, Method A) ES+ 436.0 [M+1]+.

Workup

washwashed with water (3×) and brine
dry with materialdried over Na2SO4
concentrationconcentrated under vacuum
customPurification by silica gel column chromatography (0-15% EtOAc in cyclohexane)
customtriturating with pentane

Sources & evidence

ORD record: ord-2824d84a43234a50ad907dbfc85ba251
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09302985B2

Reaction notes

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