Dichloromethane → 4-[5-(benzyloxy)pyridin-3-yl]-9H-carbazole

HRID 1877477

반응식

HRID 1877477 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](B(O)O)[CH:12]=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].ClCCl.FC(F)(F)S(O[C:33]1[C:45]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[NH:38][C:37]=2[CH:36]=[CH:35][CH:34]=1)(=O)=O>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:33]2[C:45]3[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[NH:38][C:37]=3[CH:36]=[CH:35][CH:34]=2)[CH:12]=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 53398533(5-(Benzyloxy)pyridin-3-yl)boronic acidHCID 583383234-Trifluoromethanesulphonyloxycarbazole

생성물 1

HCID 673086444-[5-(benzyloxy)pyridin-3-yl]-9H-carbazole수율 80.2%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

1.63 g of [5-(benzyloxy)pyridin-3-yl]boronic acid, 6.4 g of caesium carbonate and 0.182 g of 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride as a complex with dichloromethane (1/1) [PdCl2(dppf).CH2Cl2] are successively added, under argon, to a solution of 1.57 g of 4-trifluoromethanesulphonyloxycarbazole, obtained in stage 1 of Example 1, in a mixture of 71 ml of dioxane and 24 ml of water. The reaction mixture is refluxed for 5 hours, filtered through celite and concentrated under reduced pressure. The residue is subsequently purified by silica gel chromatography, elution being carried out with a mixture of cyclohexane and ethyl acetate (80/20 by volume), so as to give 1.4 g of 4-[5-(benzyloxy)pyridin-3-yl]-9H-carbazole in the form of a pale yellow oil, the characteristics of which are the following:

후처리

  1. temperatureThe reaction mixture is refluxed for 5 hours
  2. filtrationfiltered through celite and
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is subsequently purified by silica gel chromatography, elution
  5. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (80/20 by volume)

출처 및 근거

ORD 기록
ord-e6b179653e9f4852a66b93f250833491
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309721B2

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