Ammonium Chloride → HCID 67368547, compound

HRID 1753186Notes

Reaction equation

HRID 1753186 reaction equation
[Cl:1][C:2]([Cl:21])([Cl:20])[C:3]([C:5]1[N:6]([CH2:10][C:11]([C:13]2[CH:18]=[N:17][C:16]([CH3:19])=[CH:15][N:14]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1)=[O:4].[Br:22]N1C(=O)CCC1=O.[NH4+].[Cl-]>C1COCC1>[Br:22][C:8]1[CH:9]=[C:5]([C:3](=[O:4])[C:2]([Cl:1])([Cl:20])[Cl:21])[N:6]([CH2:10][C:11]([C:13]2[CH:18]=[N:17][C:16]([CH3:19])=[CH:15][N:14]=2)=[O:12])[CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 67184N-bromobutanimideHCID 67367061HCID 67367061, compound

Product 1

HCID 67368547HCID 67368547, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,2,2-trichloro-1-{1-[2-(5-methylpyrazin-2-yl)-2-oxoethyl]-1H-pyrrol-2-yl}ethanone (260 mg, 0.75 mmol) in THF (4.4 mL) was added N-bromosuccinimide (144 mg, 0.81 mmol) at −15° C. The mixture was allowed at room temperature overnight. A saturated aqueous solution of NH4Cl (5 mL) was added and the mixture extracted with CH2Cl2 (3×5 mL). The organics were dried (Na2SO4), filtrated and concentrated in vacuo to give a residue that was purified by chromatography (Biotage SP4, gradient 1 CV hexanes, 0-40% EtOAc in hexanes 15 CV, 40-60% 5CV) to give 1-{4-bromo-1-[2-(5-methylpyrazin-2-yl)-2-oxoethyl]-1H-pyrrol-2-yl}-2,2,2-trichloroethanone as a yellow solid (157 mg, yield: 49%).

Workup

  1. extractionthe mixture extracted with CH2Cl2 (3×5 mL)
  2. dry with materialThe organics were dried (Na2SO4)
  3. filtrationfiltrated
  4. concentrationconcentrated in vacuo
  5. customto give a residue that
  6. customwas purified by chromatography (Biotage SP4, gradient 1 CV hexanes, 0-40% EtOAc in hexanes 15 CV, 40-60% 5CV)

Sources & evidence

ORD record
ord-6948d7e849b34e1482f6d837800939dd
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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