Triethylamine → 5-Bromo-1-(ethylsulfonyl)indoline

HRID 2353454Notes

Reaction equation

HRID 2353454 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.C(N(CC)CC)C.[CH2:18]([S:20](Cl)(=[O:22])=[O:21])[CH3:19]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:20]([CH2:18][CH3:19])(=[O:22])=[O:21])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 34115665-Bromoindoline

Product 1

HCID 684261415-Bromo-1-(ethylsulfonyl)indolineYield 72.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Bromoindoline (1.98 g, 10 mmol) was dissolved in methylene chloride (100 mL) and triethylamine (4.3 mL, 30 mmol) was added. The mixture was treated with ethanesulfonyl chloride (1.41 mL, 15 mmol) and stirred for 2 hours. The mixture was diluted with methylene chloride, washed with water, 2N HCl, brine, dried over anhydrous magnesium sulfate, and concentrated. Purification via Isco chromatography (the Redisep® column, silica, 1% ethyl acetate in methylene chloride) afforded 5-bromo-1-(ethylsulfonyl)indoline (2.1 g) as a white solid. MS (EI) m/z 286.9; HPLC purity 100.0% at 210-370 nm, 10.2 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammonium formate buffer pH=3.5μ acetonitrile+MeOH) for 10 minutes, hold 4 minutes.

Workup

  1. washwashed with water, 2N HCl, brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customPurification via Isco chromatography (the Redisep® column, silica, 1% ethyl acetate in methylene chloride)

Sources & evidence

ORD record
ord-f53a967b05e74aa48b997d1edf4a0b66
Source dataset
uspto-grants-2010_07
Patent number
US07750038B2

Reaction notes

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