Sodium hydride → Ethyl 2-methyl-1-(piperidin-1-ylsulfonyl)-1H-pyrrole-3-carboxylate

HRID 1844712Notes

Reaction equation

HRID 1844712 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[H-].[Na+].[N:14]1([S:20](Cl)(=[O:22])=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>CN(C=O)C.CC(=O)OCC>[CH3:1][C:2]1[N:3]([S:20]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)(=[O:22])=[O:21])[CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 136747Ethyl 2-methyl-3-pyrrolecarboxylateHCID 11298344Piperidine-1-sulfonyl chloride

Product 1

HCID 86719130Ethyl 2-methyl-1-(piperidin-1-ylsulfonyl)-1H-pyrrole-3-carboxylateYield 79.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-methyl-1H-pyrrole-3-carboxylate (3.06 g, 20 mmol) in dry DMF (40 mL) was added NaH (0.96 mg, 24 mmol) in portions and the mixture was stirred at rt for 30 min. Then a solution of piperidine-1-sulfonyl chloride (4.4 g, 24 mmol) in dry DMF (10 mL) was added and the resulting mixture was stirred overnight, diluted with EA, washed with water and brine, dried over Na2SO4, concentrated and purified by CC (PE/EA=1/0 to 10/1) to give compound 4a (4.77 g, 78%).

Workup

  1. stirringthe resulting mixture was stirred overnight
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by CC (PE/EA=1/0 to 10/1)

Sources & evidence

ORD record
ord-7ec6badea2334c08a29f760bd758750a
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

Loading…