N,N-Dimethylglycine hydrochloride → ethyl(E)-3-(3-methoxy-4-{5-[2-(4-trifluoromethylphenyl)vinyl]pyridin-2-yloxy}phenyl)propionate

HRID 884121

反応式

Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][C:10]=2[O:22][CH3:23])=[N:6][CH:7]=1.[F:24][C:25]([F:35])([F:34])[C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[CH2:31])=[CH:28][CH:27]=1.Cl.CN(C)CC(O)=O.C([O-])(=O)C.[Na+]>C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.C(OCC)(=O)C.CN1CCCC1=O>[CH3:23][O:22][C:10]1[CH:11]=[C:12]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:13]=[CH:14][C:9]=1[O:8][C:5]1[CH:4]=[CH:3][C:2](/[CH:31]=[CH:30]/[C:29]2[CH:28]=[CH:27][C:26]([C:25]([F:24])([F:34])[F:35])=[CH:33][CH:32]=2)=[CH:7][N:6]=1

参加物

反応条件

温度: 130 °C

実験手順

To ethyl 3-[4-(5-bromopyridin-2-yloxy)-3-methoxyphenyl]propionate (610 mg, 1.6 mmol) were added 4-trifluoromethylstyrene (0.332 mL, 2.2 mmol), dichlorobis(benzonitrile)palladium(II) (33 mg, 0.082 mmol), N,N-dimethylglycine hydrochloride (17 mg, 0.16 mmol), sodium acetate (263 mg, 3.2 mmol) and N-methylpyrrolidone (5 mL) under an argon atmosphere. The resulting solution was stirred under an argon atmosphere for 17 hours at 130° C. To the reaction solution was added ethyl acetate and filtered. The filtrate was washed with water, and then dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1), to thereby yield 500 mg of the title compound.

後処理

filtrationfiltered
washThe filtrate was washed with water
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated
customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

出典と根拠

ORDレコード: ord-f82192e12f3640d09f1283cea18172f6
出典データセット: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08236826B2

反応式

参加物

反応物 4

生成物 1

試薬・触媒・溶媒 3

反応条件

実験手順

後処理

出典と根拠

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