N-bromobutanimide → Ethyl 5-bromo-2-methyl-1-(piperidin-1-ylsulfonyl)-1H-pyrrole-3-carboxylate

HRID 1844713Notes

Reaction equation

HRID 1844713 reaction equation
[CH3:1][C:2]1[N:3]([S:12]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)(=[O:14])=[O:13])[CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C1C(=O)N([Br:28])C(=O)C1>CN(C=O)C.C1COCC1.CC(=O)OCC>[Br:28][C:4]1[N:3]([S:12]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)(=[O:14])=[O:13])[C:2]([CH3:1])=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:5]=1

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 86719130Ethyl 2-methyl-1-(piperidin-1-ylsulfonyl)-1H-pyrrole-3-carboxylate

Product 1

HCID 70872970Ethyl 5-bromo-2-methyl-1-(piperidin-1-ylsulfonyl)-1H-pyrrole-3-carboxylateYield 69.6%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 4a (4.77 g, 15.9 mmol) in dry DMF (20 mL) and dry THF (20 mL) was added NBS (3.12 g, 17.5 mmol) in portions at 0° C. The mixture was stirred at rt overnight, diluted with EA, washed with water and brine, dried over Na2SO4, concentrated and purified by CC (PE/EA=1/0 to 15/1) to give compound 4b (4.2 g, 63%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by CC (PE/EA=1/0 to 15/1)

Sources & evidence

ORD record
ord-577bebad1c8e4ecb85f35198688b9b95
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

Loading…