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

HRID 389267
ノート
印刷プレビュー

反応式

HRID 389267 の反応式
Cl[C:2]1[C:7]([CH2:8][N:9]([CH2:15][CH3:16])[C:10]([CH:12]2[CH2:14][CH2:13]2)=[O:11])=[CH:6][C:5]([CH3:17])=[CH:4][N:3]=1.[CH2:18]([O:20][C:21](=[O:40])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25](B2OC(C)(C)C(C)(C)O2)[CH:24]=1)[CH3:19].C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.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>[CH2:18]([O:20][C:21](=[O:40])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([C:2]2[C:7]([CH2:8][N:9]([C:10]([CH:12]3[CH2:14][CH2:13]3)=[O:11])[CH2:15][CH3:16])=[CH:6][C:5]([CH3:17])=[CH:4][N:3]=2)[CH:24]=1)[CH3:19]
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 3

HCID 11430Potassium CarbonateHCID 58120060[4-Methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl esterHCID 58579965Cyclopropanecarboxylic acid (2-chloro-5-methyl-pyridin-3-ylmethyl)-ethyl-amide

生成物 1

HCID 58579952(3-{3-[(Cyclopropanecarbonyl-ethyl-amino)-methyl]-5-methyl-pyridin-2-yl}-4-methoxy-phenyl)-acetic acid ethyl ester

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 962Water溶媒2 回
HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

Cyclopropanecarboxylic acid (2-chloro-5-methyl-pyridin-3-ylmethyl)-ethyl-amide (0.120 g, 0.48 mmol), [4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl ester (0.183 g, 0.57 mmol), and potassium carbonate (0.198 g, 1.43 mmol) were combined in DME and H2O. The mixture was purged with N2 for 10 minutes, and then tetrakis(triphenylphosphine)palladium(0) (0.055 g, 0.05 mmol) was added, and the reaction was stirred at 80° C. for 2 hours. Once no starting material was seen by analytical tlc, the mixture was diluted with H2O and extracted three times with EtOAc. The combined organic layers were washed with H2O and brine, dried over Na2SO4, decanted, and concentrated, and the residue was purified by silica gel chromatography (0-70% EtOAc in hexanes) to give the title compound.

後処理

  1. customThe mixture was purged with N2 for 10 minutes
  2. extractionextracted three times with EtOAc
  3. washThe combined organic layers were washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. customdecanted
  6. concentrationconcentrated
  7. customthe residue was purified by silica gel chromatography (0-70% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-98893c6c89b84940ac37f893f489ec15
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08378107B2

反応ノート

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