Tributyltin Chloride → N,N-dimethyl-3-(6-methyl-3-(tributylstannyl)-1H-indazol-1-yl)propan-1-amine
反応式
I[C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH3:11])=[CH:8][CH:9]=2)[N:4]([CH2:12][CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[N:3]=1.C([Mg]Cl)(C)C.[CH2:23]([Sn:27]([CH2:33][CH2:34][CH2:35][CH3:36])([CH2:29][CH2:30][CH2:31][CH3:32])Cl)[CH2:24][CH2:25][CH3:26]>C1COCC1>[CH3:16][N:15]([CH3:17])[CH2:14][CH2:13][CH2:12][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([CH3:11])[CH:6]=2)[C:2]([Sn:27]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:23][CH2:24][CH2:25][CH3:26])=[N:3]1参加物
反応条件
- 温度
- -20 °C
実験手順
A solution of 3-(3-Iodo-6-methyl-1H-indazol-1-yl)-N,N-dimethylpropan-1-amine (480 mg, 1.4 mmol) in 20 mL of dry THF was cooled to −20° C. under nitrogen atmosphere, isopropylmagnesium chloride (1.4 mL, 2.8 mmol, 2M in THF) was added and stirred for 15 min at −20° C. Then tributylchlorostannane (0.8 mL, 2.8 mmol) was added and allowed to warm to room temperature. The reaction was cooled in an ice bath and quenched with saturated ammonium chloride solution, product extracted with ethyl acetate (3×50 mL), combined organics dried with sodium sulfate and concentrated to give 1.4 g of crude N,N-dimethyl-3-(6-methyl-3-(tributylstannyl)-1H-indazol-1-yl)propan-1-amine as an oil which was used in the next step directly without further purification.
後処理
- temperatureto warm to room temperature
- temperatureThe reaction was cooled in an ice bath
- customquenched with saturated ammonium chloride solution, product
- extractionextracted with ethyl acetate (3×50 mL)
- dry with materialcombined organics dried with sodium sulfate
- concentrationconcentrated
出典と根拠
- ORDレコード
- ord-0ddcb49aefac43e28616d696181126ec
- 出典データセット
- uspto-grants-2014_02
- 特許番号
- US08658646B2
反応ノート
読み込み中…