Hydrochloric Acid → 3-(Pyridin-4-yl)-5-(2-(quinolin-2-yl)ethyl)furo[3,2-c]pyridin-4(5H)-one

HRID 920941ノート

反応式

HRID 920941 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[N:34]1[CH:39]=[CH:38][C:37]([C:40]2[C:44]3[C:45](=[O:49])[NH:46][CH:47]=[CH:48][C:43]=3[O:42][CH:41]=2)=[CH:36][CH:35]=1.[N:50]1[C:59]2[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=2)[CH:53]=[CH:52][C:51]=1[CH2:60][CH2:61]O.Cl>C1COCC1.CC(=O)OCC>[N:34]1[CH:35]=[CH:36][C:37]([C:40]2[C:44]3[C:45](=[O:49])[N:46]([CH2:61][CH2:60][C:51]4[CH:52]=[CH:53][C:54]5[C:59](=[CH:58][CH:57]=[CH:56][CH:55]=5)[N:50]=4)[CH:47]=[CH:48][C:43]=3[O:42][CH:41]=2)=[CH:38][CH:39]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 705322-QuinolineethanolHCID 5363146Diisopropyl azodicarboxylateHCID 866831543-(Pyridin-4-yl)furo[3,2-c]pyridin-4(5H)-one

生成物 1

HCID 866831553-(Pyridin-4-yl)-5-(2-(quinolin-2-yl)ethyl)furo[3,2-c]pyridin-4(5H)-one収率 36.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
15 °C

実験手順

To a solution of triphenylphosphine (247 mg, 0.942 mmol) in THF (10 mL), DIAD (0.321 mL, 1.65 mmol) was added. The mixture was cooled to 15° C. 3-(Pyridin-4-yl)furo[3,2-c]pyridin-4(5H)-one (100 mg, 0.471 mmol) and 2-(quinolin-2-yl)ethanol from example from example a1 were added. After stirring overnight at room temperature, EA and 2M HCl were added. The phases were separated and extracted with EA. The organic phase was washed with water. The acidic aqueous phase was basified with 2M NaOH and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography to give 69 mg of the title compound (36.3%) as hydrochloride salt as dark yellow solid.

後処理

  1. customThe phases were separated
  2. extractionextracted with EA
  3. washThe organic phase was washed with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by chromatography

出典と根拠

ORDレコード
ord-4d092cf5421746948d7091afacfa9724
出典データセット
uspto-grants-2016_03
特許番号
US09273068B2

反応ノート

読み込み中…