N-bromobutanimide → HCID 89407675, compound

HRID 1524381Notes

Reaction equation

HRID 1524381 reaction equation
[CH:1]([Si:4]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([S:14]([Cl:17])(=[O:16])=[O:15])[CH:12]=2)[CH:7]=[CH:6]1)([CH3:3])[CH3:2].C1C(=O)N([Br:31])C(=O)C1>C(Cl)Cl>[Br:31][C:7]1[C:8]2[C:13](=[CH:12][C:11]([S:14]([Cl:17])(=[O:15])=[O:16])=[CH:10][CH:9]=2)[N:5]([Si:4]([CH:1]([CH3:3])[CH3:2])([CH:18]([CH3:20])[CH3:19])[CH:21]([CH3:23])[CH3:22])[CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57659737HCID 57659737, compound

Product 1

HCID 89407675HCID 89407675, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 250-mL round-bottom flask was charged with 1-(triisopropylsilyl)-1H-indole-6-sulfonyl chloride (4.2 g, 11.29 mmol) and DCM (57 ml) to give a clear, maroon solution. n-Bromosuccinimide (2.210 g, 12.42 mmol) was added in one portion, and the resulting mixture was stirred overnight. Silica gel (10.6 g) was added, and the mixture was concentrated. The impregnated silica gel was eluted onto a silica gel column with 0 to 20% EtOAc/Heptane to give to give 3-bromo-1-(triisopropylsilyl)-1H-indole-6-sulfonyl chloride (3.809 g, 8.45 mmol, 74.8% yield) as a light-yellow solid. 1H NMR (400 MHz, CDCl3) δ=8.20 (dd, J=0.4, 1.6 Hz, 1 H), 7.89-7.71 (m, 2 H), 7.55 (s, 1 H), 1.72 (quin, J=7.5 Hz, 3 H), 1.18 (d, J=7.7 Hz, 18 H).

Workup

  1. customto give a clear, maroon solution
  2. additionSilica gel (10.6 g) was added
  3. concentrationthe mixture was concentrated
  4. washThe impregnated silica gel was eluted onto a silica gel column with 0 to 20% EtOAc/Heptane
  5. customto give

Sources & evidence

ORD record
ord-2c497ceb5f43442887d839c7181639c4
Source dataset
uspto-grants-2015_07
Patent number
US09079902B2

Reaction notes

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