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 2095709ノート

反応式

HRID 2095709 の反応式
[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

参加物

6

反応物 5

HCID 8028Tetrahydrofuran2 回HCID 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、化合物

生成物 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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f8823ef991ed4909b3f6eb46479fdb26
出典データセット
uspto-grants-2013_05
特許番号
US08445510B2

反応ノート

読み込み中…