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Triphenylphosphine → 7-Bromo-5-(2-(quinolin-2-yl)ethyl)furo[3,2-c]pyridin-4(5H)-one

HRID 920936
ノート
印刷プレビュー

反応式

HRID 920936 の反応式
CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Br:34][C:35]1[C:36]2[O:44][CH:43]=[CH:42][C:37]=2[C:38](=[O:41])[NH:39][CH:40]=1.[N:45]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH:48]=[CH:47][C:46]=1[CH2:55][CH2:56]O>C1COCC1>[Br:34][C:35]1[C:36]2[O:44][CH:43]=[CH:42][C:37]=2[C:38](=[O:41])[N:39]([CH2:56][CH2:55][C:46]2[CH:47]=[CH:48][C:49]3[C:54](=[CH:53][CH:52]=[CH:51][CH:50]=3)[N:45]=2)[CH:40]=1
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 4

HCID 11776TriphenylphosphineHCID 705322-QuinolineethanolHCID 5363146Diisopropyl azodicarboxylateHCID 179855277-Bromofuro[3,2-c]pyridin-4(5H)-one

生成物 1

HCID 866831507-Bromo-5-(2-(quinolin-2-yl)ethyl)furo[3,2-c]pyridin-4(5H)-one収率 23%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

DIAD (4.91 mmol, 992 mg) was added dropwise to PPh3 (753 mg, 2.80 mmol) in 20 mL of THF. The mixture was stirred for 30 min. Then 7-bromofuro[3,2-c]pyridine-4(5H)-one (300 mg, 1.402 mmol) was added followed by the addition of 2-(quinolin-2-yl)ethanol (243 mg, 1.402 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was extracted with water/ethyl acetate. The organic phase was extracted with 1N HCl. The acidic aqueous phase was basified with 1N NaOH and extracted with DCM. The organic phase was extracted with water, dried over MgSO4, filtered, concentrated and purified by chromatography to give the title compound as white solid (119 mg, 23%).

後処理

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. extractionThe reaction mixture was extracted with water/ethyl acetate
  3. extractionThe organic phase was extracted with 1N HCl
  4. extractionextracted with DCM
  5. extractionThe organic phase was extracted with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by chromatography

出典と根拠

ORDレコード
ord-f119be6a656d4192b77628b678fac095
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09273068B2

反応ノート

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