5-Formylfuran-3-boronic acid → HCID 11590865, 화합물

HRID 1454415노트

반응식

HRID 1454415 반응식
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([C:11]([NH:19][C:20]3[CH:25]=[C:24]([O:26][CH3:27])[C:23]([Cl:28])=[CH:22][C:21]=3[Cl:29])=[C:12]([C:17]#[N:18])[CH:13]=[N:14]2)=[CH:9][C:8]=1[O:30][CH3:31])(=O)=O.[CH:34]([C:36]1[O:37][CH:38]=[C:39](B(O)O)[CH:40]=1)=[O:35]>COCCOC.C(=O)(O)[O-].[Na+]>[Cl:29][C:21]1[CH:22]=[C:23]([Cl:28])[C:24]([O:26][CH3:27])=[CH:25][C:20]=1[NH:19][C:11]1[C:10]2[C:15](=[CH:16][C:7]([C:39]3[CH:40]=[C:36]([CH:34]=[O:35])[O:37][CH:38]=3)=[C:8]([O:30][CH3:31])[CH:9]=2)[N:14]=[CH:13][C:12]=1[C:17]#[N:18]

참가 물질

5

반응물 2

HCID 52210965-Formylfuran-3-boronic acidHCID 234380223-Cyano-4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-quinolinyl trifluoromethanesulfonate

생성물 1

HCID 11590865HCID 11590865, 화합물수율 96.5%

시약·촉매·용매 2

HCID 80711,2-Dimethoxyethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

A mixture of 3-cyano-4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-quinolinyl trifluoromethanesulfonate (835 mg, 1.60 mmol), 2-formyl-4-furan boronic acid (446 mg, 3.21 mmol), and tetrakis(triphenylphosphine)pallidium (0) (20 mg) in 40 mL of ethylene glycol dimethyl ether and 25 mL of saturated aqueous sodium bicarbonate is heated at reflux for 3 hours and then cooled to room temperature. The reaction mixture is partitioned between dichloromethane and water. The aqueous layer is extracted with 10% methanol in ethyl acetate. The organic layers are combined, dried over magnesium sulfate, filtered and concentrated in vacuo. Diethyl ether is added to the residue and the solid is collected by filtration to provide 723 mg of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-(5-formyl-3-furyl)-6-methoxy-3-quinolinecarbonitrile as a light yellow solid, mp 238-241° C.; 1H NMR (DMSO-d6) δ 3.88 (s, 3H), 4.09 (s, 3H), 7.38 (s, 1H), 7.76 (s, 1H), 8.01 (s, 1H), 8.29 (broad s, 2H), 8.48 (s, 1H), 8.77 (s, 1H), 9.71 (s, 1H), 9.87 (s, 1H); MS 468.0, 470.0 (M+H)+; HRMS calcd: 468.05124, found: 468.0511 (M+H)+.

후처리

  1. temperatureis heated
  2. temperatureat reflux for 3 hours
  3. customThe reaction mixture is partitioned between dichloromethane and water
  4. extractionThe aqueous layer is extracted with 10% methanol in ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. additionDiethyl ether is added to the residue
  9. filtrationthe solid is collected by filtration

출처 및 근거

ORD 기록
ord-daec935a24104ae1a6fec31d443e094d
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07479561B2

반응 노트

불러오는 중…