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Cesium carbonate → 7-Hydroxy-4-(4-morpholin-4-yl-phenyl)-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester

HRID 642364
ノート
印刷プレビュー

反応式

HRID 642364 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10](Br)[C:9]2[S:13][C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:15][C:8]=2[C:7]=1[OH:22])=[O:5])[CH3:2].[O:23]1[CH2:28][CH2:27][N:26]([C:29]2[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=2)[CH2:25][CH2:24]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([C:32]2[CH:31]=[CH:30][C:29]([N:26]3[CH2:25][CH2:24][O:23][CH2:28][CH2:27]3)=[CH:34][CH:33]=2)[C:9]2[S:13][C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:15][C:8]=2[C:7]=1[OH:22])=[O:5])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 2795359(4-(Morpholin-4-yl)phenyl)boronic acidHCID 866173574-Bromo-7-hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester

生成物 1

HCID 684263857-Hydroxy-4-(4-morpholin-4-yl-phenyl)-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester収率 20.2%

試薬・触媒・溶媒 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
触媒
HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 4-bromo-7-hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester (230 mg, 0.61 mmole), 4-morpholinophenylboronic acid (252 mg, 1.22 mmole), cesium carbonate (596 mg, 1.83 mmole) and tetrakis(triphenylphosphine)-palladium (70 mg, 0.06 mmole) in dioxane (3 ml) was refluxed for 18 h before it was cooled to room temperature, quenched with water and filtered. The filtrate was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane to give the title compound as a white solid (57 mg). MS: (+) m/z 462.35 (M+H+)

後処理

  1. temperaturewas refluxed for 18 h before it
  2. customquenched with water
  3. filtrationfiltered
  4. customThe filtrate was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane

出典と根拠

ORDレコード
ord-36b7007609684fa992280e561386175d
出典データセット
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07696223B2

反応ノート

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