Sodium Azide → HCID 57517458, compound

HRID 1842450Notes

Reaction equation

HRID 1842450 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=[C:6]1[C:15]([O:17][CH2:18][CH3:19])=[O:16].[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C=O)C.O.CCOC(C)=O>[N:20]([CH2:2][CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=[C:6]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N+:21]=[N-:22]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 57517457HCID 57517457, compound

Product 1

HCID 57517458HCID 57517458, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of crude diethyl 1-(3-bromopropyl)-1H-pyrrole-2,4-dicarboxylate in DMF (30 mL) was added sodium azide (1 g, 15.4 mmol). The resulting mixture was stirred at rt overnight then diluted with water (30 mL) and EtOAc (150 mL). After separation, the aqueous layer was extracted with EtOAc (2×150 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-(3-azidopropyl)-1H-pyrrole-2,4-dicarboxylate (2 g, 75%). 1H NMR (CDCl3, 300 MHz) δ7.42 (s, 1H), 7.36 (s, 1 H), 4.40 (t, J=6.6 Hz, 2 H), 4.26 (m, 4 H), 3.30 (m, J=6.2 Hz, 2 H), 2.04 (m, 2 H), 1.36 (m, 6 H).

Workup

  1. customAfter separation
  2. extractionthe aqueous layer was extracted with EtOAc (2×150 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-6b483604b9504614bb4428e47e92cb23
Source dataset
uspto-grants-2015_02
Patent number
US08946223B2

Reaction notes

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