4-Nitrobenzenesulfonyl chloride → 4-Bromo-1-[(4-nitrophenyl)sulfonyl]-1H-indole-6-carbonitrile

HRID 520598

Reaction equation

HRID 520598 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.[N+:31]([C:34]1[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1)([O-:33])=[O:32]>CN(C)C=O>[Br:1][C:2]1[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[S:40]([C:37]1[CH:36]=[CH:35][C:34]([N+:31]([O-:33])=[O:32])=[CH:39][CH:38]=1)(=[O:41])=[O:42]

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 247288834-bromo-1H-indole-6-carbonitrile

Product 1

HCID 666922724-Bromo-1-[(4-nitrophenyl)sulfonyl]-1H-indole-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-1H-indole-6-carbonitrile (207 mg), PS-BEMP (900 mg) and 4-nitrobenzenesulfonyl chloride (380 mg) were weighed to a round bottom flask, then N,N-Dimethylformamide (4 ml) was added and the reaction was stirred at RT. The reaction was filtered and washed with DMF. The DMF was evaporated and the residue was dissolved in DCM:methanol and passed through a 5 g SAX cartridge (preconditioned with methanol) washing with DCM:methanol. The residue was evaporated to afford the title compound, 360 mg as a pale orange solid.

Workup

  1. filtrationThe reaction was filtered
  2. washwashed with DMF
  3. customThe DMF was evaporated
  4. dissolutionthe residue was dissolved in DCM
  5. washwashing with DCM
  6. customThe residue was evaporated

Sources & evidence

ORD record
ord-b012c838402e4d64b66e3aab0f2606b9
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Linked notes

Loading…