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 2095639ノート

反応式

HRID 2095639 の反応式
[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

参加物

5

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 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、化合物

生成物 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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5e7ece3f85c641d380dc18ae4f67260c
出典データセット
uspto-grants-2013_05
特許番号
US08445510B2

反応ノート

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