Sodium Hydroxide → HCID 68712618, compound

HRID 1159773Notes

Reaction equation

HRID 1159773 reaction equation
[OH-].[Na+].Cl.[N:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10](Cl)(=[O:12])=[O:11])[CH:5]=1.[Br:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH:17]=[CH:18][NH:19]2>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Br:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH:17]=[CH:18][N:19]2[S:10]([C:6]1[CH:5]=[N:4][CH:9]=[CH:8][CH:7]=1)(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 6764944-BromoindoleHCID 12571517Pyridine-3-sulfonyl chloride hydrochloride2×

Product 1

HCID 68712618HCID 68712618, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

Aq. 2M NaOH (1 mL) was added to a stirred mixture of pyridine-3-sulfonyl chloride hydrochloride (240 mg, 1.12 mmol; Intermediate 23), 4-bromoindole (200 mg, 1.02 mmol) and tetrabutylammonium hydrogen sulfate (35 mg, 0.10 mmol). The reaction was stirred 45 min. and the layers were allowed to separate. The organic layer was washed twice with diluted aq. NaOH, dried and concentrated to get the title compound (325 mg, 95%) as an off white solid. MS (ESI+) for C13H9BrN2O2S m/z 337 (M+H)+.

Workup

  1. customto separate
  2. washThe organic layer was washed twice with diluted aq. NaOH
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9f993f898dd0403996746e906b6f3782
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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