Tetrahydrofuran → 1-(5,8-dioxaspiro[3.4]oct-2-yl)-5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 2095709노트

반응식

HRID 2095709 반응식
[CH2:1]1[C:4]2([O:8][CH2:7][CH2:6][O:5]2)[CH2:3][CH:2]1[N:9]1[C:13]([CH3:14])=[C:12](I)[CH:11]=[N:10]1.C1COCC1.C([Mg]Cl)(C)C.CO[B:28]1[O:32][C:31]([CH3:34])([CH3:33])[C:30]([CH3:36])([CH3:35])[O:29]1.[NH4+].[Cl-]>>[CH2:1]1[C:4]2([O:8][CH2:7][CH2:6][O:5]2)[CH2:3][CH:2]1[N:9]1[C:13]([CH3:14])=[C:12]([B:28]2[O:32][C:31]([CH3:34])([CH3:33])[C:30]([CH3:36])([CH3:35])[O:29]2)[CH:11]=[N:10]1

참가 물질

6

반응물 5

HCID 8028Tetrahydrofuran2회HCID 25517Ammonium ChlorideHCID 109757592-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 585160751-(5,8-dioxaspiro[3.4]oct-2-yl)-4-iodo-5-methyl-1H-pyrazoleHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 670044581-(5,8-dioxaspiro[3.4]oct-2-yl)-5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

실험 절차

To a solution of 1-(5,8-dioxaspiro[3.4]oct-2-yl)-4-iodo-5-methyl-1H-pyrazole (50.0 mg, 0.156 mmol) in THF (3 mL, 40 mmol) at was added 2 M isopropylmagnesium chloride in THF (0.23 mL, 0.46 mmol), and the mixture was stirred at rt for 1 h. The reaction was quenched with 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.10 mL, 0.62 mmol) and allowed to stir at rt for 1 h. Sat. NH4Cl was added, and the organic solvent was removed in vacuo. The material was extracted with DCM and water. The organic layer was concentrated in vacuo to afford the title compound as a white solid. The material was used in the next step without further purification.

후처리

  1. stirringto stir at rt for 1 h
  2. customthe organic solvent was removed in vacuo
  3. extractionThe material was extracted with DCM and water
  4. concentrationThe organic layer was concentrated in vacuo

출처 및 근거

ORD 기록
ord-f8823ef991ed4909b3f6eb46479fdb26
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445510B2

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