Triisopropyl borate → (5-Cyano-1-benzothiophen-2-yl)boronic acid

HRID 2173025노트

반응식

HRID 2173025 반응식
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([C:10]#[N:11])[CH:8]=[CH:9][C:2]1=2.C([Li])CCC.[B:17](OC(C)C)([O:22]C(C)C)[O:18]C(C)C>C1COCC1>[C:10]([C:7]1[CH:8]=[CH:9][C:2]2[S:1][C:5]([B:17]([OH:22])[OH:18])=[CH:4][C:3]=2[CH:6]=1)#[N:11]

참가 물질

5

반응물 3

HCID 21531Triisopropyl borateHCID 27954521-Benzothiophene-5-carbonitrileHCID 178418339Butyllithium

생성물 1

HCID 53398611(5-Cyano-1-benzothiophen-2-yl)boronic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a cold (−78° C.) solution of benzo[b]thiophene-5-carbonitrile (276 mg, 1.734 mmol) in anhydrous THF (5 mL) was added n-butyllithium (0.763 mL, 1.907 mmol) dropwise. The reaction mixture was stirred at −78° C. for 60 minutes. Next, a solution of triisopropyl borate (0.478 mL, 2.080 mmol) was added. The reaction mixture was stirred for 30 minutes stirring at −78° C. and then was allowed to warm to room temperature over a 2 hour period. Solvent was removed to give the title compound, which was used without purification or work up.

후처리

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. stirringstirring at −78° C.
  3. temperatureto warm to room temperature over a 2 hour period
  4. customSolvent was removed

출처 및 근거

ORD 기록
ord-c964ed1377204c2e9b6f5bd9586267cd
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056873B2

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