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Water → Methyl 5-(benzyloxy)-6-(2-fluoro-5-methoxyphenyl)nicotinate

HRID 709796
ノート
印刷プレビュー

反応式

HRID 709796 の反応式
[CH2:1]([O:8][C:9]1[C:10](Cl)=[N:11][CH:12]=[C:13]([CH:18]=1)[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[CH2:1]([O:8][C:9]1[C:10]([C:22]2[CH:23]=[C:24]([O:27][CH3:28])[CH:25]=[CH:26][C:21]=2[F:20])=[N:11][CH:12]=[C:13]([CH:18]=1)[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 41572112-Fluoro-5-methoxyphenylboronic acidHCID 71496987Methyl 5-(benzyloxy)-6-chloronicotinate

生成物 1

HCID 117760070Methyl 5-(benzyloxy)-6-(2-fluoro-5-methoxyphenyl)nicotinate収率 95.5%

試薬・触媒・溶媒 2

HCID 178477754
HCID 178477754、化合物
触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

Under a nitrogen atmosphere, to a solution of methyl 5-(benzyloxy)-6chloronicotinate (2.77 g) in 1,4-dioxane (100 mL) were added 2-fluoro-5methoxyphenylboronic acid (2.00 g), potassium carbonate (2.76 g), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (36 mg) and water (10 mL), and the mixture was stirred at 80° C. for 20 hr. The reaction mixture was concentrated, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to give the title compound (3.50 g) as a colorless oil.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate)

出典と根拠

ORDレコード
ord-8f1257b230414b179698f89fa52ea2b6
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181186B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート