Hydrochloric Acid → HCID 118432106, compound

HRID 2207910Notes

Reaction equation

HRID 2207910 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=3[F:19])[N:10]=[C:9]([CH:20]=[O:21])[CH2:8]2)=[CH:4][CH:3]=1.[C:22]([Si](C)(C)C)([F:25])([F:24])[F:23].Cl>O1CCCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[Br:1][C:2]1[S:6][C:5]([CH:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=3[F:19])[N:10]=[C:9]([CH:20]([OH:21])[C:22]([F:25])([F:24])[F:23])[CH2:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 118431980HCID 118431980, compound

Product 1

HCID 118432106HCID 118432106, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 2724141Tetrabutylammonium FluorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(5-bromo-thiophen-2-yl)-1-(2,4-difluoro-phenyl)-4,5-dihydro-1H-pyrazole-3-carbaldehyde (9.1 g, 22.4 mmol) prepared in Step 5 and CF3TMS (5.7 mL, 38.1 mmol) in tetrahydrofuran (100.0 mL), was slowly added a solution of TBAF (1.0 M, in tetrahydrofuran 0.5 mL, 0.5 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1 hour and then a 6N hydrochloric acid solution was added thereto. The reaction mixture was stirred at room temperature for 1 hour and then extracted with ethyl acetate. The extract was washed distilled water and brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 9.9 g of the titled compound as a yellow liquid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed
  4. distillationdistilled water and brine
  5. dry with materialdried on anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d7e81be0adee42699d929ff06844ade4
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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