Methanol → HCID 59887419, compound

HRID 2353456Notes

Reaction equation

HRID 2353456 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.[CH:11]([S:14](Cl)(=[O:16])=[O:15])([CH3:13])[CH3:12].CO>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:14]([CH:11]([CH3:13])[CH3:12])(=[O:16])=[O:15])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 887MethanolHCID 824082-Propanesulfonyl chlorideHCID 34115665-Bromoindoline

Product 1

HCID 59887419HCID 59887419, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

5-Bromoindoline (0.59 g, 3 mmol) was dissolved in isopropylsulfonyl chloride (1.08 g, 7.5 mmol) and heated to 100° C. for 3 hours. The mixture was cooled and treated with methanol (10 mL) then diluted with ethyl acetate. The mixture was washed with NaHCO3, water, brine, dried over anhydrous magnesium sulfate, and concentrated. Purification via Isco chromatography (the Redisep® column, silica, gradient 5%-30% ethyl acetate in hexane) afforded 5-bromo-1-(isopropylsulfonyl)indoline (0.3 g) as a white solid. MS (EI) m/z 303.7; HPLC purity 95.8% at 210-370 nm, 9.6 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammonium formate buffer pH=3.5 acetonitrile+MeOH) for 10 minutes, hold 4 minutes.

Workup

  1. temperatureThe mixture was cooled
  2. washThe mixture was washed with NaHCO3, water, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customPurification via Isco chromatography (the Redisep® column, silica, gradient 5%-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-e9794f57b6a348e5ab49997371471ec2
Source dataset
uspto-grants-2010_07
Patent number
US07750038B2

Reaction notes

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