Ammonia → 4-Bromo-1H-pyrrole-2-carboxamide

HRID 1056295Notes

Reaction equation

HRID 1056295 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:7](=[O:12])C(Cl)(Cl)Cl)[NH:5][CH:6]=1.[NH3:13]>CC#N>[Br:1][C:2]1[CH:3]=[C:4]([C:7]([NH2:13])=[O:12])[NH:5][CH:6]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 27981401-(4-bromo-1H-pyrrol-2-yl)-2,2,2-trichloroethanone

Product 1

HCID 153468234-Bromo-1H-pyrrole-2-carboxamideYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 1-(4-bromo-1H-pyrrol-2-yl)-2,2,2-trichloroethanone (CombiBlocks, Inc., San Diego, Calif.; 1.50 g, 5.15 mmol) and ammonia (30 wt. % in water; 4.0 mL, 55.5 mmol) in CH3CN (62.5 mL) was stirred at 23° C. for 45 min. The reaction mixture was then concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-100% EtOAc/hexanes) furnished 4-bromo-1H-pyrrole-2-carboxamide (885 mg, 4.68 mmol, 91% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.75 (1H, br. s.), 7.55 (1H, br. s.), 7.08 (1H, br. s.), 6.95 (1H, dd, J=2.8, 1.7 Hz), 6.84 (1H, dd, J=2.4, 1.7 Hz). 13C NMR (100 MHz, DMSO-d6) δ ppm 161.1, 126.9, 121.2, 112.0, 94.8. m/z (ESL+ve) 188.9/190.9 (M+H)+.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customChromatographic purification of the residue (silica gel, 0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f7a48040f260471eb075ceccdaab6999
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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