Triethylamine → perfluorophenyl 3-bromo-1-methyl-1H-indole-6-sulfonate

HRID 1524386Notes

Reaction equation

HRID 1524386 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([S:11](Cl)(=[O:13])=[O:12])=[CH:8][CH:9]=2)[N:4]([CH3:15])[CH:3]=1.[F:16][C:17]1[C:22]([OH:23])=[C:21]([F:24])[C:20]([F:25])=[C:19]([F:26])[C:18]=1[F:27].C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([S:11]([O:23][C:22]3[C:21]([F:24])=[C:20]([F:25])[C:19]([F:26])=[C:18]([F:27])[C:17]=3[F:16])(=[O:13])=[O:12])=[CH:8][CH:9]=2)[N:4]([CH3:15])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13041PentafluorophenolHCID 894076923-Bromo-1-methyl-1H-indole-6-sulfonyl chloride

Product 1

HCID 89407702perfluorophenyl 3-bromo-1-methyl-1H-indole-6-sulfonateYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A vial was charged with 3-bromo-1-methyl-1H-indole-6-sulfonyl chloride (505.0 mg, 1.637 mmol), pentafluorophenol (452 mg, 2.455 mmol), and DCM (8.1 mL) to give a clear, light-yellow solution. Triethylamine (342 μl, 2.455 mmol) was added dropwise, and the resulting mixture was stirred for 45 min before being concentrated in vacuo. The crude product was purified by chromatography on silica gel (40% EtOAc/Heptane) to give perfluorophenyl 3-bromo-1-methyl-1H-indole-6-sulfonate (712.3 mg, 1.561 mmol, 95% yield) as an off-white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ=8.04 (t, J=1.1 Hz, 1 H), 7.82-7.67 (m, 2 H), 7.41 (s, 1 H), 3.91 (s, 3 H).

Workup

  1. customto give a clear, light-yellow solution
  2. concentrationbefore being concentrated in vacuo
  3. customThe crude product was purified by chromatography on silica gel (40% EtOAc/Heptane)

Sources & evidence

ORD record
ord-a1c1c1623e3d4841a8e14ad999a98a0b
Source dataset
uspto-grants-2015_07
Patent number
US09079902B2

Reaction notes

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