Trichloroacetyl chloride → HCID 86657087, compound

HRID 1910960Notes

Reaction equation

HRID 1910960 reaction equation
[N:1]1([CH2:6][C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][N:10]=2)=[O:8])[CH:5]=[CH:4][CH:3]=[CH:2]1.[Cl:19][C:20]([Cl:25])([Cl:24])[C:21](Cl)=[O:22]>C(Cl)Cl>[Cl:19][C:20]([Cl:25])([Cl:24])[C:21]([C:2]1[N:1]([CH2:6][C:7](=[O:8])[C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:11][N:10]=2)[CH:5]=[CH:4][CH:3]=1)=[O:22]

Participants

4

Reactant 2

HCID 6420Trichloroacetyl chlorideHCID 67366260HCID 67366260, compound

Product 1

HCID 86657087HCID 86657087, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a chilled (0° C.) solution of the 2-(1H-pyrrol-1-yl)-1-[5-(trifluoromethyl)pyridin-2-yl]ethanone (100 mg, approx. 90% pure, 0.35 mmol) in dry CH2Cl2 (5 mL) was added trichloroacetyl chloride (90 μL, 0.80 mmol) under nitrogen. The mixture was allowed to warm to room temperature. After completion (44 hours, monitored by LCMS) the mixture was cooled to 0° C. and quenched with a saturated aqueous solution of NaHCO3 (5 mL). The aqueous layer was then extracted with CH2Cl2 (2×2 mL). The organic layers were combined, dried (MgSO4), filtered and concentrated in vacuo to yield a residue that was purified by flash chromatography (Biotage, 12 g cartridge, gradient hexanes 1 CV, 0-60% EtOAc in hexanes 10 CV) to give 2,2,2-trichloro-1-(1-{2-oxo-2-[5-(trifluoromethyl)pyridin-2-yl]ethyl}-1H-pyrrol-2-yl)ethanone as an orange oil (105 mg, yield: 75%). ESI-MI m/z [M+H]+ 398.9.

Workup

  1. temperatureAfter completion (44 hours, monitored by LCMS) the mixture was cooled to 0° C.
  2. customquenched with a saturated aqueous solution of NaHCO3 (5 mL)
  3. extractionThe aqueous layer was then extracted with CH2Cl2 (2×2 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a residue that
  8. customwas purified by flash chromatography (Biotage, 12 g cartridge, gradient hexanes 1 CV, 0-60% EtOAc in hexanes 10 CV)

Sources & evidence

ORD record
ord-1e5e0b1ee42340ef908c5ff4cad12c5e
Source dataset
uspto-grants-2013_12
Patent number
US08604034B2

Reaction notes

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