反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.CC([O-])(C)C.[K+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[F:62][C:63]1[CH:68]=[CH:67][C:66]([NH:69][CH3:70])=[CH:65][CH:64]=1>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:62][C:63]1[CH:68]=[CH:67][C:66]([N:69]([CH3:70])[C:2]2[CH:7]=[N:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)=[CH:65][CH:64]=1参加物
実験手順
According to Scheme 22 Method B: To a mixture of 5-bromo-2-methoxypyridine (1 eq, 1.06 mmol, 0.14 mL), KOtBu (1.5 eq, 1.60 mmol, 0.18 g), Pd(OAc)2 (0.02 eq, 21 μmol, 48 mg), BINAP (0.04 eq, 42 μmol, 26 mg) in degassed DMF (1.5 mL) was added 4-fluoro-N-methylbenzenamine (1.2 eq, 1.28 mmol, 0.14 mL). The reaction mixture was microwaved at 130° C. for 5 min. The reaction mixture was quenched with water and the aqueous phase was extracted with AcOEt. The organic fraction washed brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 15 g SiO2, CH2Cl2/AcOEt 90/10) to afford N-(4-fluorophenyl)-6-methoxy-N-methylpyridin-3-amine (0.08 mmol, 20 mg, 8%) as a yellow oil.
後処理
- customThe reaction mixture was microwaved at 130° C. for 5 min
- customThe reaction mixture was quenched with water
- extractionthe aqueous phase was extracted with AcOEt
- washThe organic fraction washed brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 15 g SiO2, CH2Cl2/AcOEt 90/10)
出典と根拠
- ORDレコード
- ord-0ac0dac57ae7483bb5880c6c3bad3dc0
- 出典データセット
- uspto-grants-2013_03
- 特許番号
- US08399493B2
関連ノート
読み込み中…