4-Fluorophenylboronic acid → [7-(4-Fluoro-phenyl)-4-methoxy-benzooxazol-2-yl]-carbamic acid methyl ester

HRID 1611948ノート

反応式

HRID 1611948 の反応式
[CH3:1][O:2][C:3](=[O:17])[NH:4][C:5]1[O:6][C:7]2[C:13](I)=[CH:12][CH:11]=[C:10]([O:15][CH3:16])[C:8]=2[N:9]=1.[Cl-].[Li+].[F:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C(=O)(O)[O-].[Na+]>O1CCOCC1.COCCOC>[CH3:1][O:2][C:3](=[O:17])[NH:4][C:5]1[O:6][C:7]2[C:13]([C:24]3[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=3)=[CH:12][CH:11]=[C:10]([O:15][CH3:16])[C:8]=2[N:9]=1

参加物

7

反応物 4

HCID 2856454-Fluorophenylboronic acidHCID 433294Lithium ChlorideHCID 516892Sodium BicarbonateHCID 23593642(7-Iodo-4-methoxy-benzooxazol-2-yl)-carbamic acid methyl ester

生成物 1

HCID 69288206[7-(4-Fluoro-phenyl)-4-methoxy-benzooxazol-2-yl]-carbamic acid methyl ester収率 98%

試薬・触媒・溶媒 2

HCID 80711,2-Dimethoxyethane溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of 3.00 g (8.62 mmol) (7-iodo-4-methoxy-benzooxazol-2-yl)-carbamic acid methyl ester in 20 ml dioxane and 60 ml 1,2-dimethoxyethane were added 731 mg (17.2 mmol) lithium chloride, 299 mg (0.26 mmol) tetrakis(triphenyl-phosphine)palladium(0), 1.45 g (10.3 mmol) para-fluorobenzeneboronic acid and 18 ml of a 1 N aq. solution of sodium bicarbonate. The mixture was heated at 100° C. for 24 h and then poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Trituration in ether afforded 2.67 g (98%) [7-(4-fluoro-phenyl)-4-methoxy-benzooxazol-2-yl]-carbamic acid methyl ester as an off-white solid. ES-MS m/e (%): 317 (M+H+, 100).

後処理

  1. additionpoured onto water
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-fe8ce4dcce184b8883c3347b16d85a35
出典データセット
uspto-grants-2006_01
特許番号
US06992083B2

反応ノート

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