Hydrochloric Acid → 1-(2,3-Dihydro-[1,4]dioxino[2,3-b]pyridin-7-yl)ethan-1-one

HRID 1038584ノート

反応式

HRID 1038584 の反応式
Br[C:2]1[CH:3]=[C:4]2[O:11][CH2:10][CH2:9][O:8][C:5]2=[N:6][CH:7]=1.[CH2:12]([O:14]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:13].Cl>C1(C)C=CC=CC=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>[O:11]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:12](=[O:14])[CH3:13])[CH:3]=2)[O:8][CH2:9][CH2:10]1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 133540297-bromo-2H,3H-[1,4]dioxino[2,3-b]pyridine

生成物 1

HCID 665985031-(2,3-Dihydro-[1,4]dioxino[2,3-b]pyridin-7-yl)ethan-1-one収率 69%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

Under an argon atmosphere, 7-bromo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine (65 mg, 0.30 mmol) was dissolved in toluene (1.5 mL), added tetrakis(triphenylphosphine)palladium (35 mg, 0.03 mmol) and 1-ethoxyethenyl tri n-butyl tin (112 ΞL, 0.33 mmol), and the mixture was stirred at 100° C. overnight. The reaction solution was reverted to room temperature, and added 1N hydrochloric acid. The reaction solution was filtered through a pad of celite. The reaction solution was added ethyl acetate for extraction. The organic layer was washed with brine, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by preparative thin-layer chromatography (n-hexane/ethyl acetate=1/1). The title compound (37 mg (yield 69%)) was obtained as a white solid.

後処理

  1. customwas reverted to room temperature
  2. filtrationThe reaction solution was filtered through a pad of celite
  3. additionThe reaction solution was added ethyl acetate
  4. extractionfor extraction
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. custompurified by preparative thin-layer chromatography (n-hexane/ethyl acetate=1/1)

出典と根拠

ORDレコード
ord-4bf9fc92f3c143c6a96324bd6b516291
出典データセット
uspto-grants-2013_10
特許番号
US08551985B2

反応ノート

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