N-bromobutanimide → 5-Bromo-N-(tert-butyl)-1-(cyclohexylmethyl)-1H-pyrrole-3-sulfonamide

HRID 1844745Notes

Reaction equation

HRID 1844745 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:28])C(=O)C1>C1COCC1>[Br:28][C:12]1[N:11]([CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:10]=[C:9]([S:6]([NH:5][C:1]([CH3:4])([CH3:2])[CH3:3])(=[O:8])=[O:7])[CH:13]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86719140N-(tert-Butyl)-1-(cyclohexylmethyl)-1H-pyrrole-3-sulfonamide

Product 1

HCID 867191415-Bromo-N-(tert-butyl)-1-(cyclohexylmethyl)-1H-pyrrole-3-sulfonamideYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of compound 27e (280 mg, 0.94 mmol) in dry THF (3 mL) was added NBS (200 mg, 1.13 mmol) at −78° C. and the solution was stirred at this temperature for 30 min, quenched with water and extracted with EA twice. The combined organic layers were washed with water (3×) and brine, concentrated and purified by CC (PE/EA=5/1) to give compound 27f (300 mg, 85%) as an oil.

Workup

  1. customquenched with water
  2. extractionextracted with EA twice
  3. washThe combined organic layers were washed with water (3×) and brine
  4. concentrationconcentrated
  5. custompurified by CC (PE/EA=5/1)

Sources & evidence

ORD record
ord-0ffc69c3bcb64032bb271df9625b403c
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

Loading…