Triisopropyl borate → HCID 86718552, compound

HRID 1485030Notes

Reaction equation

HRID 1485030 reaction equation
I[C:2]1[CH:3]=[N:4][N:5]([CH3:14])[C:6]=1[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Li]CCCC.[B:20](OC(C)C)([O:25]C(C)C)[O:21]C(C)C>C1COCC1>[CH3:14][N:5]1[C:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:2]([B:20]([OH:25])[OH:21])[CH:3]=[N:4]1

Participants

5

Reactant 3

HCID 21531Triisopropyl borateHCID 86718553HCID 86718553, compoundHCID 178418339Butyllithium

Product 1

HCID 86718552HCID 86718552, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

4-Iodo-1-methyl-5-phenoxy-1H-pyrazole (862.00 mg; 2.75 mmol) was dissolved in 15 ml THF extra dry and cooled down to −78° C. Afterwards was added n-BuLi (1.80 ml; 2.88 mmol; 1.6 mol/1 in Hexane) and Triisopropyl borate (982.28 mg; 5.22 mmol). It was stirred for 1 hour. The reaction mixture was quenched with 1 ml water and purified with reversed phase chromatography under basic conditions.

Workup

  1. customdry
  2. customThe reaction mixture was quenched with 1 ml water
  3. custompurified with reversed phase chromatography under basic conditions

Sources & evidence

ORD record
ord-1ddd3bb62ddc476fa777ad8232ffcae1
Source dataset
uspto-grants-2016_08
Patent number
US09422290B2

Reaction notes

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