反応式
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][CH:3]=1.[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[C:16](B(O)O)[CH:15]=[CH:14][N:13]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].CC(O)CC>[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[C:16]([C:2]2[CH:3]=[CH:4][C:5]([CH2:8][NH2:9])=[CH:6][N:7]=2)[CH:15]=[CH:14][N:13]=1参加物
反応物 4
生成物 1
試薬・触媒・溶媒 2
反応条件
- 温度
- 100 °C
実験手順
To a flask containing (6-chloropyridin-3-yl)methanamine 33-2 (375 mg, 2.63 mmol), 2-(trifluoromethyl)pyridin-4-ylboronic acid 33-1 (500 mg, 2.63 mmol), Pd(OAc)2 (34 mg, 0.15 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos) (124 mg, 0.30 mmol) and potassium phosphate (1.90 g, 9.00 mmol) under argon was added 2-butanol (4 mL). The mixture was stirred at 100° C. for 10 hours. After cooling to room temperature, the mixture was filtered through celite cake. The filtrate was diluted with ethyl acetate, washed with H2O and brine, dried over Na2SO4, and concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, eluted with 5% methanol containing ˜7N ammonia in dichloromethane to give (2′-(trifluoromethyl)-2,4′-bipyridin-5-yl)methanamine 33-3 as a yellow solid. MS m/z 254.1 (M+1)
後処理
- temperatureAfter cooling to room temperature
- filtrationthe mixture was filtered through celite cake
- additionThe filtrate was diluted with ethyl acetate
- washwashed with H2O and brine
- dry with materialdried over Na2SO4
- concentrationconcentrated to dryness by rotary evaporation
- customThe crude product was purified by silica gel flash chromatography
- washeluted with 5% methanol containing ˜7N ammonia in dichloromethane
出典と根拠
- ORDレコード
- ord-3bcf7431285b4be586bd389a0b629ac8
- 出典データセット
- uspto-grants-2015_11
- 特許番号
- US09181235B2
関連ノート
読み込み中…