1,4-Dimethylpyrazole → 1,4-dimethyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 589045노트

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HRID 589045 반응식
[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[CH:4]=[N:3]1.C([Li])CCC.C(O[B:17]1[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18]1)(C)C>C1COCC1.CCOC(C)=O>[CH3:1][N:2]1[C:6]([B:17]2[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18]2)=[C:5]([CH3:7])[CH:4]=[N:3]1

참가 물질

6

반응물 3

HCID 1368361,4-DimethylpyrazoleHCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178418339Butyllithium

생성물 1

HCID 578266761,4-dimethyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

1,4-Dimethyl-1H-pyrazole (50 mg, 0.5 mmol) was stirred in THF (2 mL) and cooled to 0° C. A solution of 1.6 M n-butyllithium in hexanes (390 mL) was added dropwise by syringe and the mixture was allowed to warm to room temperature for 2 h. The mixture was cooled to −78° C. and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (110 mL, 0.52 mmol) was added dropwise by syringe. The mixture was stirred at −78° C. for 15 min. and at 0° C. for 3 h. The mixture was diluted with EtOAc and washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by chromatography on silica gel using EtOAc in hexanes gave the sub-title compound. LCMS calc. for C11H20BN2O2 (M+H)+: m/z=223.2. found: 223.0.

후처리

  1. temperatureto warm to room temperature for 2 h
  2. temperatureThe mixture was cooled to −78° C.
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by chromatography on silica gel

출처 및 근거

ORD 기록
ord-90d264228a804bfbabedb89e1d5a4ecd
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227985B2

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