Hydrochloric Acid → HCID 58572760、化合物

HRID 1920807ノート

反応式

HRID 1920807 の反応式
Br[C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([O:10][CH3:11])[C:3]=1[NH2:4].C([Sn](CCCC)(CCCC)[C:17]([O:19]CC)=[CH2:18])CCC.Cl>O1CCOCC1>[NH2:4][C:3]1[C:5]([O:10][CH3:11])=[CH:6][C:7]([F:9])=[CH:8][C:2]=1[C:17](=[O:19])[CH3:18]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 585727442-Bromo-4-fluoro-6-methoxybenzenamine

生成物 1

HCID 58572760HCID 58572760、化合物収率 70%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a solution of 2-bromo-4-fluoro-6-methoxy aniline (4.80 g, 21.8 mmol), which had been obtained in Reference example 5 (5a), in 1,4-dioxane (200 mL), tributyl (1-ethoxy vinyl) tin (11.1 mL, 32.7 mmol) and tetrakistriphenyl phosphine palladium (2.52 g, 2.18 mmol) were added, and the mixture was stirred for 16 hours at 100° C. After cooling the reaction solution to room temperature, 1 N aqueous hydrogen chloride solution (100 mL) was added and stirred further for 2 hours. The reaction solution was concentrated under reduced pressure, neutralized by adding 1 N aqueous sodium hydroxide solution, and then extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate=4/1) to give the title compound as a yellow solid substance (2.80 g, yield 70%).

後処理

  1. temperatureAfter cooling the reaction solution to room temperature
  2. stirringstirred further for 2 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionby adding 1 N aqueous sodium hydroxide solution
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel chromatography (n-hexane/ethyl acetate=4/1)

出典と根拠

ORDレコード
ord-b5236c50f6bf4232a15a7a410cb611d4
出典データセット
uspto-grants-2012_05
特許番号
US08173631B2

反応ノート

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