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Potassium Carbonate → (5-{2-[(Benzyl-cyclopropanecarbonyl-amino)-methyl]-4-cyano-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

HRID 554592
ノート
印刷プレビュー

反応式

HRID 554592 の反応式
[CH2:1]([N:8]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:16]=1B1OC(C)(C)C(C)(C)O1)[C:9]([CH:11]1[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:32]([O:34][C:35](=[O:44])[CH2:36][C:37]1[CH:38]=[N:39][CH:40]=[C:41](Br)[CH:42]=1)[CH3:33].C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:32]([O:34][C:35](=[O:44])[CH2:36][C:37]1[CH:38]=[N:39][CH:40]=[C:41]([C:16]2[CH:17]=[CH:18][C:19]([C:21]#[N:22])=[CH:20][C:15]=2[CH2:14][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]([CH:11]2[CH2:12][CH2:13]2)=[O:10])[CH:42]=1)[CH3:33]
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

8

反応物 3

HCID 11430Potassium CarbonateHCID 54116619Ethyl 2-(5-bromopyridin-3-yl)acetateHCID 67212390Cyclopropanecarboxylic acid benzyl-[5-cyano-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-amide

生成物 1

HCID 67212964(5-{2-[(Benzyl-cyclopropanecarbonyl-amino)-methyl]-4-cyano-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

試薬・触媒・溶媒 4

HCID 178418397
HCID 178418397、化合物
触媒
HCID 313Hydrochloric Acid溶媒
HCID 962Water溶媒
HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
70 °C

実験手順

Cyclopropanecarboxylic acid benzyl-[5-cyano-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-amide (1.33 g, 3.2 mmol), (5-bromo-pyridin-3-yl)-acetic acid ethyl ester (1.02 g, 4.2 mmol), and potassium carbonate (1.55 g, 11.2 mmol) were combined in DME (40 mL) and H2O (30 mL), and the solution was purged with N2 for 15 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.370 g, 0.35 mmol) was added, and the reaction was stirred at 70° C. for 1 hour. The mixture was diluted with H2O and 1N aqueous HCl (15 mL), and extracted with EtOAc. The combined organic layers were concentrated and purified by preparative HPLC to give (5-{2-[(benzyl-cyclopropanecarbonyl-amino)-methyl]-4-cyano-phenyl}-pyridin-3-yl)-acetic acid ethyl ester, as well as the some of the hydrolyzed ester product.

後処理

  1. customH2O (30 mL), and the solution was purged with N2 for 15 minutes
  2. extractionextracted with EtOAc
  3. concentrationThe combined organic layers were concentrated
  4. custompurified by preparative HPLC

出典と根拠

ORDレコード
ord-bb027aabd8bb46da8616333f5d0354e0
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08049015B2

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