Potassium Carbonate → HCID 71143849, compound

HRID 2173043Notes

Reaction equation

HRID 2173043 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=O)[NH:5][CH:6]=1.Br[CH2:10]/[CH:11]=[CH:12]/[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[N:5]([CH:6]=1)[CH:10]=[CH:11][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5996274-Bromo-1H-pyrrole-2-carbaldehydeHCID 5373944Ethyl (E)-4-bromobut-2-enoate

Product 1

HCID 71143849HCID 71143849, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-bromo-1H-pyrrole-2-carbaldehyde (1.00 g, 5.75 mmol), (E)-ethyl 4-bromobut-2-enoate (1.555 mL, 11.49 mmol), and potassium carbonate (1.74 g, 12.6 mmol) in DMF (20 mL) was stirred overnight at room temperature under a nitrogen atmosphere. Following reaction, the solution was extracted with ethyl acetate (2×100 mL) and water (100 mL). The organic layers were combined, dried over sodium sulfate, concentrated, and purified via silica gel flash chromatography, eluting with a gradient of 10-30% EtOAc and hexane to give, upon removal of solvent, the title compound as a purple solid (350 mg, 23%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.32 (t, J=7.40 Hz, 3H), 4.31 (q, J=5.40 Hz, 2H), 6.92 (s, 1H), 7.02-7.03 (m, 1H), 7.93 (s, 1H), 8.13 (s, 1H), 8.28-8.29 (m, 1H). ESI-MS m/z [M+H]+ calc'd for C11H10BrNO2, 268. found, 268.

Workup

  1. customreaction
  2. extractionthe solution was extracted with ethyl acetate (2×100 mL) and water (100 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified via silica gel flash chromatography
  6. washeluting with a gradient of 10-30% EtOAc and hexane
  7. customto give, upon removal of solvent

Sources & evidence

ORD record
ord-d5d76fccb479420d862e01e98a62953c
Source dataset
uspto-grants-2015_06
Patent number
US09056873B2

Reaction notes

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