Potassium Carbonate → Methyl 3-(3-pyridinyl)benzoate

HRID 880253ノート

反応式

HRID 880253 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1)=[O:4].Br[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[C:3]([O:2][CH3:1])=[O:4])[CH:16]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 122863-BromopyridineHCID 312751,4-DioxaneHCID 27347143-(Methoxycarbonyl)benzeneboronic acid

生成物 1

HCID 4133188Methyl 3-(3-pyridinyl)benzoate収率 90%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

A mixture of (3-(methoxycarbonyl)phenyl)boronic acid (600 mg, 3.33 mmol), 3-bromopyridine (479 mg, 3.0 mmol), K2CO3 (1.2 g, 9.0 mmol) and Pd(dppf)Cl2 (50 mg) in a solution of dioxane (10 mL) and H2O (2.5 mL) was stirred at 120° C. for 30 minutes with microwave heating under N2. The catalyst was then filtered and the filtrate concentrated. The residue was then purified by column chromatography to give the desired product and used directly in the next step. (630 mg Yield 90%).

後処理

  1. temperaturewith microwave heating under N2
  2. filtrationThe catalyst was then filtered
  3. concentrationthe filtrate concentrated
  4. customThe residue was then purified by column chromatography

出典と根拠

ORDレコード
ord-1847187d0eac452281a98d3d17245484
出典データセット
uspto-grants-2015_03
特許番号
US08993555B2

反応ノート

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