Sodium Azide → diethyl 1-(2-azidoethyl)-1H-pyrrole-2,4-dicarboxylate

HRID 1842447Notes

Reaction equation

HRID 1842447 reaction equation
Br[CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[C:5]1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C.O.CCOC(C)=O>[N:19]([CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[C:5]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N+:20]=[N-:21]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 18967495diethyl 1-(2-bromoethyl)-1H-pyrrole-2,4-dicarboxylate

Product 1

HCID 57517455diethyl 1-(2-azidoethyl)-1H-pyrrole-2,4-dicarboxylateYield 57%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of diethyl 1-(2-bromoethyl)-1H-pyrrole-2,4-dicarboxylate (0.8 g) in DMF (10 mL) was added sodium azide (0.2 g, 3.07 mmol). The resulting mixture was stirred at rt overnight then diluted with water (10 mL) and EtOAc (100 mL). After separation, the aqueous layer was extracted with EtOAc (2×50 mL). The combined organic layers were washed with brine, dried (MgSO4) and concentrated. Purification via flash chromatography (petroleum ether:EtOAc, 20:1 to 15:1) afforded diethyl 1-(2-azidoethyl)-1H-pyrrole-2,4-dicarboxylate (0.4 g, 57%). 1H NMR (CDCl3, 300 MHz) δ7.49 (d, J=1.8 Hz, 1 H), 7.43 (d, J=1.8 Hz, 1 H), 4.88 (t, J=5.5 Hz, 2 H), 4.32 (q, J=7.2 Hz, 4 H), 3.70 (t, J=6.4 Hz, 2 H), 1.38 (m, 6 H).

Workup

  1. customAfter separation
  2. extractionthe aqueous layer was extracted with EtOAc (2×50 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification via flash chromatography (petroleum ether:EtOAc, 20:1 to 15:1)

Sources & evidence

ORD record
ord-79863ced30614442a65b7b6b0c39d718
Source dataset
uspto-grants-2015_02
Patent number
US08946223B2

Reaction notes

Loading…