Sodium hydride → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-1H-pyrazole
反応式
Br[CH2:2][C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[CH3:13][C:14]1([CH3:26])[C:18]([CH3:20])([CH3:19])[O:17][B:16]([C:21]2[CH:22]=[N:23][NH:24][CH:25]=2)[O:15]1.[H-].[Na+]>CN(C)C=O>[CH3:13][C:14]1([CH3:26])[C:18]([CH3:19])([CH3:20])[O:17][B:16]([C:21]2[CH:25]=[N:24][N:23]([CH2:2][C:3]34[CH2:12][CH:7]5[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]5)[CH2:4]3)[CH2:10]4)[CH:22]=2)[O:15]1参加物
5
反応条件
- 温度
- 0 °C
実験手順
A mixture of 1-(bromomethyl)adamantane (0.458 g) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.377 g) in N,N-dimethylformamide (5 mL) was cooled to 0° C. To this solution was added 60% sodium hydride (0.096 g). The solution was heated at 70° C. overnight. The reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 25% ethyl acetate in hexanes to provide the title compound.
後処理
- temperatureThe solution was heated at 70° C. overnight
- customThe reaction mixture was partitioned between water and ethyl acetate
- extractionThe aqueous layer was extracted with additional ethyl acetate twice
- washThe combined organic layers were washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash column chromatography on silica gel eluting with 25% ethyl acetate in hexanes
出典と根拠
- ORDレコード
- ord-9cc8de4df8764f2d9025e7d5839024a4
- 出典データセット
- uspto-grants-2016_01
- 特許番号
- US09227963B2
反応ノート
読み込み中…