Tetrahydrofuran → 1-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 2095639노트

반응식

HRID 2095639 반응식
[CH3:1][C:2]1([CH3:16])[O:6][C@H:5]([CH2:7][N:8]2[C:12]([CH3:13])=[C:11](I)[C:10]([CH3:15])=[N:9]2)[CH2:4][O:3]1.C1COCC1.C([Mg]Cl)(C)C.CO[B:29]1[O:33][C:32]([CH3:35])([CH3:34])[C:31]([CH3:37])([CH3:36])[O:30]1>>[CH3:1][C:2]1([CH3:16])[O:6][C@H:5]([CH2:7][N:8]2[C:12]([CH3:13])=[C:11]([B:29]3[O:33][C:32]([CH3:35])([CH3:34])[C:31]([CH3:37])([CH3:36])[O:30]3)[C:10]([CH3:15])=[N:9]2)[CH2:4][O:3]1

참가 물질

5

반응물 4

HCID 8028Tetrahydrofuran2회HCID 109757592-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 670042591-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-4-iodo-3,5-dimethyl-1H-pyrazoleHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 670044181-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

실험 절차

To a solution of 1-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-4-iodo-3,5-dimethyl-1H-pyrazole (180.0 mg, 0.5354 mmol) in THF (5 mL, 60 mmol) was added 2 M isopropylmagnesium chloride in THF (0.5354 mL, 1.071 mmol) at rt, and the mixture was stirred for 10 min. 2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.2632 mL, 1.606 mmol) was added, and the mixture stirred at rt for 20 min. The reaction was quenched with sat. NH4Cl, and the organic solvent was removed in vacuo. The material was extracted with DCM and water, and the organic layer was concentrated in vacuo to afford the title compound as a clear oil. The material was used in the next step without further purification.

후처리

  1. stirringthe mixture stirred at rt for 20 min
  2. customThe reaction was quenched with sat. NH4Cl
  3. customthe organic solvent was removed in vacuo
  4. extractionThe material was extracted with DCM and water
  5. concentrationthe organic layer was concentrated in vacuo

출처 및 근거

ORD 기록
ord-5e7ece3f85c641d380dc18ae4f67260c
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445510B2

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