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Ethyl Acetate → (6-chloro-5-{2-[(N-cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

HRID 554621
ノート
印刷プレビュー

反応式

HRID 554621 の反応式
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([Cl:13])=[C:10](Br)[CH:11]=1)[CH3:2].[CH2:15]([N:17]([CH2:23][C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:25]=1B1OC(C)(C)C(C)(C)O1)[C:18]([CH:20]1[CH2:22][CH2:21]1)=[O:19])[CH3:16].C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>COCCOC.[Cl-].[Na+].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.O>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([Cl:13])=[C:10]([C:25]2[CH:26]=[CH:27][C:28]([C:30]([F:33])([F:32])[F:31])=[CH:29][C:24]=2[CH2:23][N:17]([C:18]([CH:20]2[CH2:22][CH2:21]2)=[O:19])[CH2:15][CH3:16])[CH:11]=1)[CH3:2]
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

9

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 58565131HCID 58565131、化合物HCID 66607375Cyclopropanecarboxylic acid ethyl-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-benzyl]-amide

生成物 1

HCID 86640538(6-chloro-5-{2-[(N-cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
85 °C

実験手順

(5-Bromo-6-chloro-pyridin-3-yl)-acetic acid ethyl ester (0.549 g, 1.97 mmol), cyclopropanecarboxylic acid ethyl-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-benzyl]-amide (0.787 g, 1.97 mmol), and potassium carbonate (0.824 g, 5.91 mmol) were combined in DME (6 mL) and H2O (3 mL), and the solution was purged with N2 for 40 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.338 g, 0.20 mmol) was added, and the reaction was stirred at 85° C. for 2 hours. After cooling to room temperature, the mixture was worked-up with EtOAc, H2O, and brine, and the organic layer was separated, dried, filtered, and concentrated. The residue was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give (6-chloro-5-{2-[(N-cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid ethyl ester.

後処理

  1. customH2O (3 mL), and the solution was purged with N2 for 40 minutes
  2. temperatureAfter cooling to room temperature
  3. customthe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (0-100% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-0033d9b8852848f6969734e31e3cbacd
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