Ethyl Acetate → HCID 59526026, compound

HRID 385929Notes

Reaction equation

HRID 385929 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[N:11]=2)[CH:7]=[N:6]1.[H-].C([Al+]CC(C)C)C(C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+].C(OCC)(=O)C>O1CCCC1>[Br:16][C:12]1[N:11]=[C:10]([C:8]2[CH:7]=[N:6][N:5]([CH2:4][CH2:3][OH:2])[CH:9]=2)[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9855836Potassium sodium tartarateHCID 21225700Diisobutylaluminumhydride2×HCID 59526011HCID 59526011, compound

Product 1

HCID 59526026HCID 59526026, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of methyl[4-(6-bromopyridin-2-yl)-1H-pyrazol-1-yl]acetate (196 mg, 0.66 mmol) in tetrahydrofuran (3.4 mL) was added diisobutylaluminum hydride (1.0M in hexane, 1.99 mL, 1.99 mmol) dropwise. The solution was allowed to warm to room temperature and maintained at room temperature overnight. Additional diisobutylaluminum hydride (0.66 mL, 0.66 mmol) was then added and the reaction was stirred for another 24 hours. Saturated aqueous potassium sodium tartrate (20 mL) was then added and the solution was vigorously stirred for three hours. Ethyl acetate (7 mL) was added to the solution, and it was stirred another 60 minutes. The organic layer was separated and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (0-5% methanol in ethyl acetate) afforded the title compound.

Workup

  1. temperaturemaintained at room temperature overnight
  2. stirringthe solution was vigorously stirred for three hours
  3. stirringwas stirred another 60 minutes
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted three times with ethyl acetate
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification via silica gel chromatography (0-5% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-52508431442b41258cb05afc71ec07ea
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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