1-Bromo-2-methylpropane → HCID 89484222, compound

HRID 1746401Notes

Reaction equation

HRID 1746401 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=2[CH3:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:21](N=C(N(C)C)N(C)C)([CH3:24])([CH3:23])[CH3:22].BrCC(C)C>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:12]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=2[CH3:20])[CH2:22][CH:21]([CH3:24])[CH3:23])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 89479805HCID 89479805, compound

Product 1

HCID 89484222HCID 89484222, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-fluoro-N-[2-methyl-5-(methyloxy)phenyl]benzenesulfonamide (185.8 mg, 0.629 mmol) in Acetonitrile (5 mL) was added neat Barton's base (2-(tert-butyl)-1,1,3,3-tetramethylguanidine) (0.131 mL, 0.629 mmol). The reaction mixture was stirred at room temperature for 1 hour. 1-bromo-2-methylpropane (0.137 mL, 1.258 mmol) was then added. The reaction vessel was sealed and heated in Biotage Initiator microwave using initial high absorbance power setting to 150° C. for 25 min. The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus. The sample was loaded in dichloromethane and purified on automated normal chromatograph on silica (Si) 50 g using a 0-50% ethyl acetate-cyclohexane over 40 mins. The appropriate fractions were combined and dried under a stream of nitrogen in the Radleys blowdown apparatus to give the required product 171 mg as a white solid.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureheated in Biotage Initiator microwave
  3. waitsetting to 150° C. for 25 min
  4. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus
  5. custompurified on automated normal chromatograph on silica (Si) 50 g
  6. customover 40 mins
  7. customdried under a stream of nitrogen in the Radleys blowdown apparatus

Sources & evidence

ORD record
ord-da5543d9cb3240a09299e69b42e437af
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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