1-Bromo-2-methylpropane → HCID 86721893, compound

HRID 1049049Notes

Reaction equation

HRID 1049049 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:20])(=[O:19])[NH:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.Br[CH2:23][CH:24]([CH3:26])[CH3:25].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:20])(=[O:19])[N:11]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:23][CH:24]([CH3:26])[CH3:25])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 26486858HCID 26486858, compound

Product 1

HCID 86721893HCID 86721893, compoundYield 143.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(4-fluoro-phenylsulfamoyl)-benzoic acid methyl ester (1.00 g, 3.23 mmol), 1-bromo-2-methyl propane (527 μL, 4.85 mmol), and K2CO3 (891 mg, 6.46 mmol) in DMF (10 mL) was heated at 90° C. for 18 hours. The cooled mixture was diluted with EtOAc, washed with water and brine, dried over Na2SO4 and concentrated under vacuum. Purification by silica gel column chromatography (0-50% EtOAc in cyclohexane) gave 4-[(4-fluoro-phenyl)-isobutyl-sulfamoyl]-benzoic acid methyl ester (1.69 g, 77%). 1H NMR (300 MHz, CDCl3) δ 8.12 (d, J=8.3 Hz, 2H), 7.63 (d, J=8.3 Hz, 2H), 6.99 (d, J=6.5 Hz, 4H), 3.96 (s, 3H), 3.31 (d, J=7.3 Hz, 2H), 1.58-1.56 (m, 1H), 0.92 (d, J=6.7 Hz, 6H). LCMS (m/z, Method A) ES+ 366.1 [M+1]+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customPurification by silica gel column chromatography (0-50% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-fedd0566b1fb4fad958b0df3f3935fa7
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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