N-bromobutanimide → 3-Bromo-1-methyl-1H-indole-6-sulfonyl chloride

HRID 1524384Notes

Reaction equation

HRID 1524384 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([S:11]([Cl:14])(=[O:13])=[O:12])[CH:9]=2)[CH:4]=[CH:3]1.C1C(=O)N([Br:22])C(=O)C1>C(Cl)Cl>[Br:22][C:4]1[C:5]2[C:10](=[CH:9][C:8]([S:11]([Cl:14])(=[O:13])=[O:12])=[CH:7][CH:6]=2)[N:2]([CH3:1])[CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 594057661-methyl-1H-indole-6-sulfonyl chloride

Product 1

HCID 894076923-Bromo-1-methyl-1H-indole-6-sulfonyl chlorideYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-methyl-1H-indole-6-sulfonyl chloride (8.764 g, 38.2 mmol) in DCM (190 ml) was treated with n-bromosuccinimide (7.47 g, 42.0 mmol). The resulting mixture was stirred in the dark for 2.5 h, then filtered through a silica gel pad. The filter pad was washed with DCM (2×), and the filtrates were combined. The combined solution was concentrated to give 3-bromo-1-methyl-1H-indole-6-sulfonyl chloride (11.562 g, 37.5 mmol, 98% yield) as an orange solid. 1H NMR (400 MHz, CDCl3) δ=8.08 (dd, J=0.4, 1.7 Hz, 1 H), 7.87-7.80 (m, 1 H), 7.79-7.70 (m, 1 H), 7.42 (s, 1 H), 3.93 (s, 3 H).

Workup

  1. filtrationfiltered through a silica gel pad
  2. washThe filter pad was washed with DCM (2×)
  3. concentrationThe combined solution was concentrated

Sources & evidence

ORD record
ord-b1543daa5da44888a38c6a32558972a3
Source dataset
uspto-grants-2015_07
Patent number
US09079902B2

Reaction notes

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