2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 1-(3-{[tert-butyl(dimethyl)silyl]oxy}cyclobutyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 511273노트

반응식

HRID 511273 반응식
C([Mg]Cl)(C)C.[C:6]([Si:10]([CH3:23])([CH3:22])[O:11][CH:12]1[CH2:15][CH:14]([N:16]2[CH:20]=[C:19](I)[CH:18]=[N:17]2)[CH2:13]1)([CH3:9])([CH3:8])[CH3:7].CO[B:26]1[O:30][C:29]([CH3:32])([CH3:31])[C:28]([CH3:34])([CH3:33])[O:27]1>C1COCC1>[Si:10]([O:11][CH:12]1[CH2:15][CH:14]([N:16]2[CH:20]=[C:19]([B:26]3[O:30][C:29]([CH3:32])([CH3:31])[C:28]([CH3:34])([CH3:33])[O:27]3)[CH:18]=[N:17]2)[CH2:13]1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:23])[CH3:22]

참가 물질

5

반응물 3

HCID 109757592-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 672531081-[3-(tert-butyl-dimethyl-silanyloxy)-cyclobutyl]-4-iodo-1H-pyrazole2회HCID 178418918HCID 178418918, 화합물

생성물 1

HCID 672540531-(3-{[tert-butyl(dimethyl)silyl]oxy}cyclobutyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

Over the course of 5 minutes, a 2.00 M solution of isopropylmagnesium chloride in THF (0.13084 mL, 0.26168 mmol) was added dropwise to an ice cooled solution of 1-[3-(tert-butyl-dimethyl-silanyloxy)-cyclobutyl]-4-iodo-1H-pyrazole (Compound 100B, 30.00 mg, 0.07930 mmol) in THF (0.33 mL). The reaction mixture was stirred at 0° C. for another hour. 2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.057933 mL, 0.33939 mmol) was added at 0° C. and then the mixture was stirred at rt for another hour. The reaction mixture was cooled back down to 0° C., quenched with saturated aqueous NH4Cl, and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to dryness, giving the title compound as a colorless oil. Compound was taken on for the next step without further purification. MS (ES+): m/z 379.04 (100) [MH+]; HPLC: tR=3.85 min (ZQ3, polar—5 min).

후처리

  1. stirringthe mixture was stirred at rt for another hour
  2. temperatureThe reaction mixture was cooled back down to 0° C.
  3. customquenched with saturated aqueous NH4Cl
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to dryness

출처 및 근거

ORD 기록
ord-d8c9958cd0494b0093bed2e661a400dc
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096624B2

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