Triisopropyl borate → HCID 22032084, compound

HRID 1792424Notes

Reaction equation

HRID 1792424 reaction equation
Br[C:2]1[C:3]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[N:4][N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1.C([Li])CCC.[B:38](OC(C)C)([O:43]C(C)C)[O:39]C(C)C.[Cl-].[NH4+]>O1CCCC1.CCCCCC.O>[F:32][C:29]1[CH:30]=[CH:31][C:26]([C:3]2[C:2]([B:38]([OH:43])[OH:39])=[CH:6][N:5]([C:7]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:4]=2)=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 21531Triisopropyl borateHCID 25517Ammonium ChlorideHCID 22031528HCID 22031528, compoundHCID 178418339Butyllithium

Product 1

HCID 22032084HCID 22032084, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

47.5 g 4-bromo-3-(4-fluorophenyl)-1-trityl-1H-pyrazole was dissolved in 400 mL anhydrous tetrahydrofuran, and then 40.7 mL solution of 1.6 M n-butyl lithium in hexane was added dropwise thereto at −70° C. The mixture was stirred for 30 minutes, 17.2 mL triisopropyl borate was added dropwise thereto, and the mixture was stirred at −70° C. for 1 hour and at −40° C. for 1 hour. The temperature was increased to 0° C., 50 mL aqueous saturated ammonium chloride solution was added thereto and stirred for 30 minutes, and water was added to the reaction solution which was then extracted with ethyl acetate. The extract was dried over magnesium sulfate, the solvent was removed under reduced pressure, and upon addition of toluene to the resulting oil, colorless crystals were formed. The crystals were collected by filtration, to give 31 g of the title compound.

Workup

  1. customat −70° C
  2. stirringthe mixture was stirred at −70° C. for 1 hour and at −40° C. for 1 hour
  3. stirringstirred for 30 minutes
  4. extractionwas then extracted with ethyl acetate
  5. dry with materialThe extract was dried over magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. additionupon addition of toluene to the resulting oil
  8. customcolorless crystals were formed
  9. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-f80513410356425d8f6b7c43ded5850e
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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