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Potassium Carbonate → 7-(2,2-Dimethyl-propionyloxy)-4-(3-methoxy-phenyl)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester

HRID 2388144
ノート
印刷プレビュー

反応式

HRID 2388144 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9](Br)[C:8]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:14][C:7]=2[C:6]=1[O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[O:4].[CH3:28][O:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(OCC)(=O)C.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>[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9]([C:34]2[CH:33]=[CH:32][CH:31]=[C:30]([O:29][CH3:28])[CH:35]=2)[C:8]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:14][C:7]=2[C:6]=1[O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[O:4].[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9]([C:34]2[CH:33]=[CH:32][CH:31]=[C:30]([O:29][CH3:28])[CH:35]=2)[C:8]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:14][C:7]=2[C:6]=1[OH:21])=[O:4]
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 2734370(3-Methoxyphenyl)boronic acidHCID 866481124-Bromo-7-(2,2-dimethyl-propionyloxy)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester

生成物 2

HCID 675295117-(2,2-Dimethyl-propionyloxy)-4-(3-methoxy-phenyl)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester
HCID 67530551
7-Hydroxy-4-(3-methoxy-phenyl)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

Under a nitrogen atmosphere 4-bromo-7-(2,2-dimethyl-propionyloxy)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester (51 mg, 0.12 mmol), 3-methoxyphenylboronic acid (21.5 mg, 0.14 mmol), potassium carbonate (58.7 mg, 0.43 mmol), and tetrakis(triphenylphosphine)palladium(0) (20.4 mg, 0.018 mmol) were suspended in 3 mL of anhydrous 1,4-dioxane. The reaction mixture was heated at 100° C. for 16 hours, then cooled to room temperature, and diluted with ethyl acetate. The mixture was successively washed with water, saturated sodium bicarbonate, and brine solutions. The organic fraction was dried over anhydrous sodium sulfate and concentrated. The residue was purified by flash chromatography eluting from silica gel with a gradient of 0-50% ethyl acetate in hexanes to give 7.5 mg of 7-(2,2-Dimethyl-propionyloxy)-4-(3-methoxy-phenyl)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester and 24.7 mg of 7-hydroxy-4-(3-methoxy-phenyl)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester.

後処理

  1. temperaturecooled to room temperature
  2. washThe mixture was successively washed with water, saturated sodium bicarbonate, and brine solutions
  3. dry with materialThe organic fraction was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting from silica gel with a gradient of 0-50% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-adb1fb5ff8b44d0dbc54177f64566cb5
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08269008B2

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