Triisopropyl borate → HCID 22031399, compound

HRID 1792425Notes

Reaction equation

HRID 1792425 reaction equation
C([Mg]Br)(C)C.I[C:7]1[C:8]([C:31]2[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][CH:32]=2)=[N:9][N:10]([C:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=1.[B:39](OC(C)C)([O:44]C(C)C)[O:40]C(C)C.[Cl-].[NH4+]>O1CCCC1>[C:35]([C:34]1[CH:33]=[CH:32][C:31]([C:8]2[C:7]([B:39]([OH:44])[OH:40])=[CH:11][N:10]([C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:9]=2)=[CH:38][CH:37]=1)#[N:36]

Participants

6

Reactant 4

HCID 21531Triisopropyl borateHCID 25517Ammonium ChlorideHCID 22031835HCID 22031835, compoundHCID 178418365HCID 178418365, compound

Product 1

HCID 22031399HCID 22031399, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

17.2 mL of 0.75 M isopropyl magnesium bromide was added dropwise at −40° C. into a solution of 6 g 4-(4-iodo-1-trityl-1H-3-pyrazolyl)benzonitrile in tetrahydrofuran, and the mixture was stirred for 30 minutes. Subsequently, 3.3 mL triisopropyl borate was added dropwise thereto at −40° C. ad stirred at −10° C. for 2 hours. The temperature of the reaction mixture was raised to room temperature, 20 mL saturated ammonium chloride solution was added thereto, and the mixture was stirred for 30 minutes. After extraction with ethyl acetate, the organic layer was washed with water and brine and dried over magnesium sulfate, and the solvent was removed. By recrystallization from toluene/hexane (2:1), 3.45 g of the title compound was obtained as colorless crystals.

Workup

  1. stirringat −40° C. ad stirred at −10° C. for 2 hours
  2. stirringthe mixture was stirred for 30 minutes
  3. extractionAfter extraction with ethyl acetate
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was removed
  7. customBy recrystallization from toluene/hexane (2:1)

Sources & evidence

ORD record
ord-e067988a14f641bf928dd0855ddf7da7
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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