Trichloroacetyl chloride → HCID 67367061, compound

HRID 1753185Notes

Reaction equation

HRID 1753185 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]([C:8](=[O:15])[CH2:9][N:10]2[CH:14]=[CH:13][CH:12]=[CH:11]2)=[N:6][CH:7]=1.[Cl:16][C:17]([Cl:22])([Cl:21])[C:18](Cl)=[O:19].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:16][C:17]([Cl:22])([Cl:21])[C:18]([C:14]1[N:10]([CH2:9][C:8]([C:5]2[CH:4]=[N:3][C:2]([CH3:1])=[CH:7][N:6]=2)=[O:15])[CH:11]=[CH:12][CH:13]=1)=[O:19]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 67367315HCID 67367315, compound

Product 1

HCID 67367061HCID 67367061, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a chilled (0° C.) solution of 1-(5-methylpyrazin-2-yl)-2-(1H-pyrrol-1-yl)ethanone (318 mg, 1.58 mmol) in CH2Cl2 (21 mL) was added 2,2,2-trichloroacetyl chloride (400 μL, 3.56 mmol). The solution was allowed at room temperature and stirred until complete (overnight, monitored by LCMS). A chilled saturated solution of NaHCO3(15 mL) was then added and the mixture extracted with CH2Cl2 (3×15 mL). The organic were dried (Na2SO4), filtrated and concentrated in vacuo to give a residue that is purified by flash chromatography (Biotage SP4, 4 g cartridge, gradient 1 CV hexane, 0-50% EtOAc in hexanes 10 CV; 50-100% 3CV). The compound 2,2,2-Trichloro-1-{1-[2-(5-methylpyrazin-2-yl)-2-oxoethyl]-1H-pyrrol-2-yl}ethanone was isolated as a crystalline solid (260 mg, yield 38%). 1H-NMR (400 MHz, CDCl3): δ 2.70 (s, 3H), 5.91 (2H, s), 6.45 (dd, 1H, J 4.4, 2.5, Hz), 7.02 (dd, 1H, J 2.4, 1.6 Hz), 7.64 (dd, 1H, J 4.4, 1.5 Hz), 8.53-8.55 (m, 1H), 9.15 (d, 1H, J 1.3 Hz).

Workup

  1. customwas allowed at room temperature
  2. extractionthe mixture extracted with CH2Cl2 (3×15 mL)
  3. dry with materialThe organic were dried (Na2SO4)
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo
  6. customto give a residue that
  7. customis purified by flash chromatography (Biotage SP4, 4 g cartridge, gradient 1 CV hexane, 0-50% EtOAc in hexanes 10 CV; 50-100% 3CV)

Sources & evidence

ORD record
ord-92b21dcd621b4629b9397effa71c73d4
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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