Trichloroacetyl chloride → 2,2,2-Trichloro-1-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]ethanone

HRID 880014Notes

Reaction equation

HRID 880014 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:12]=[C:13]3[CH:19]=[CH:18][NH:17][C:14]3=[N:15][CH:16]=2)[CH:8]=[N:7]1.[Cl:20][C:21]([Cl:26])([Cl:25])[C:22](Cl)=[O:23]>ClC(Cl)C>[Cl:20][C:21]([Cl:26])([Cl:25])[C:22]([C:19]1[C:13]2[C:14](=[N:15][CH:16]=[C:11]([C:9]3[CH:8]=[N:7][N:6]([CH3:5])[CH:10]=3)[CH:12]=2)[NH:17][CH:18]=1)=[O:23]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 580861115-(1-Methyl-1H-pyrazol-4-YL)-1H-pyrrolo[2,3-B]pyridine

Product 1

HCID 678146252,2,2-Trichloro-1-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]ethanone

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

76.3 g of AlCl3 are suspended in 600 ml of dichloroethane under argon, and 22.7 g of the product 2 prepared above are incorporated in portions. During this addition, the orange solution changes colour to dark brown. After 10 min, 19.2 ml of trichloroacetyl chloride are slowly added dropwise. The reaction batch is cooled here using a water bath. When the addition is complete, the mixture is stirred at RT for a further 6 h before the suspension is filtered off with suction and the filter cake is washed with dichloromethane and water. The filter cake is transferred into a flask, and water is carefully added with ice-water cooling. The beige solid is filtered off with suction, likewise rinsed and subsequently dried at 70° C. in a vacuum drying cabinet for 3 h, giving 20.6 g. The acidic mother liquor is poured into ice-water, the suspension is likewise filtered off with suction as described above and dried, giving 10.3 g. The mother liquor is left to stand for 12 h, and precipitated product is filtered off with suction and dried, giving 0.4 g. The solids are combined; HPLC-MS: Rt=2.132 min; [M+H+]: 345.0.

Workup

  1. additionDuring this addition
  2. temperatureThe reaction batch is cooled here
  3. additionWhen the addition
  4. filtrationis filtered off with suction
  5. washthe filter cake is washed with dichloromethane and water
  6. customThe filter cake is transferred into a flask
  7. additionwater is carefully added with ice-water cooling
  8. filtrationThe beige solid is filtered off with suction
  9. washlikewise rinsed
  10. customsubsequently dried at 70° C. in a vacuum
  11. customdrying cabinet for 3 h
  12. customgiving 20.6 g
  13. filtrationthe suspension is likewise filtered off with suction
  14. customdried
  15. customgiving 10.3 g
  16. waitThe mother liquor is left
  17. waitto stand for 12 h
  18. customprecipitated product
  19. filtrationis filtered off with suction
  20. customdried
  21. customgiving 0.4 g

Sources & evidence

ORD record
ord-6f8704b69ffc4f6386aeb858224b4e1b
Source dataset
uspto-grants-2015_03
Patent number
US08993564B2

Reaction notes

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