Hydrochloric Acid → HCID 66697803, compound

HRID 340597Notes

Reaction equation

HRID 340597 reaction equation
[F:1][C:2]1[C:7]([N:8]2[C:12]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=3)(=[O:15])=[O:14])=[CH:11][C:10]([C:23](OCC)=[O:24])=[N:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1.C1(C)C=CC=CC=1>[F:1][C:2]1[C:7]([N:8]2[C:12]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=3)(=[O:15])=[O:14])=[CH:11][C:10]([CH2:23][OH:24])=[N:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 66697820HCID 66697820, compound

Product 1

HCID 66697803HCID 66697803, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of ethyl 1-(2-fluoropyridin-3-yl)-5-[(3-methylphenyl)sulfonyl]-1H-pyrazole-3-carboxylate (384 mg) in tetrahydrofuran (5 mL) was cooled to −78° C., a 1.5 mol/L solution (2.6 mL) of diisobutylaluminum hydride in toluene was added dropwise. The reaction mixture was stirred for 1 hr at 0° C., treated with 1 mol/L hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound as a colorless oil (yield 320 mg, yield 94%)

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-91d44a243faf42b6822fae9854e1afb8
Source dataset
uspto-grants-2014_11
Patent number
US08895588B2

Reaction notes

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