Cesium fluoride → Methyl 2'-fluoro-5'-(methyloxy)-2-(tetrahydro-2H-pyran-2-yloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662340

反応式

HRID 1662340 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1B(O)O.[F-].[Cs+].Br[C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=1[O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1>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.COCCOC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=1[O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1

参加物

6

反応物 3

HCID 25953Cesium fluorideHCID 41572112-Fluoro-5-methoxyphenylboronic acidHCID 16747841Methyl 4-bromo-3-(tetrahydropyran-2-yloxy)benzoate

生成物 1

HCID 57707262Methyl 2'-fluoro-5'-(methyloxy)-2-(tetrahydro-2H-pyran-2-yloxy)-1,1'-biphenyl-4-carboxylate収率 71.8%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

To a 2 dram vial charged with 2-fluoro-5-methoxyphenylboronic acid (available from Aldrich) (3.17 g, 18.7 mmol), tetrakis(triphenylphosphine)palladium (0) (0.719 g, 0.622 mmol), cesium fluoride (1.15 mL, 31.1 mmol), and 26.2 (1.96 g, 6.22 mmol), was added DME (20 mL). The reaction mixture was then heated at 90° C. overnight. The reaction was allowed to cool and then filtered and concentrated. The crude product was purified by combiflash (0 to 10% EtOAc/hexanes) yielding 26.3 (1.61 g, 71.8% yield).

後処理

  1. temperatureto cool
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe crude product was purified by combiflash (0 to 10% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-72bfed00d73443308d9f04a6536efbb6
出典データセット
uspto-grants-2011_10
特許番号
US08030354B2

関連ノート

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