Cesium carbonate → 2-(3-(9-Ethyl-9H-imidazo[4,5-c]pyridazin-6-yl)phenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine

HRID 1846038노트

반응식

HRID 1846038 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([B:15]3[NH:26][C:25]4[C:27]5[C:21]([CH:22]=[CH:23][CH:24]=4)=[CH:20][CH:19]=[CH:18][C:17]=5[NH:16]3)[CH:12]=[CH:13][CH:14]=2)O1.Cl[C:30]1[C:31]2[N:38]=[CH:37][N:36]([CH2:39][CH3:40])[C:32]=2[N:33]=[N:34][CH:35]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.[Pd](Cl)Cl.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2]>[CH2:39]([N:36]1[C:32]2[N:33]=[N:34][CH:35]=[C:30]([C:9]3[CH:10]=[C:11]([B:15]4[NH:26][C:25]5[C:27]6[C:21]([CH:22]=[CH:23][CH:24]=5)=[CH:20][CH:19]=[CH:18][C:17]=6[NH:16]4)[CH:12]=[CH:13][CH:14]=3)[C:31]=2[N:38]=[CH:37]1)[CH3:40]

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 552967654-chloro-7-ethyl-7H-imidazo(4,5-c)pyridazineHCID 71306573M-Benzenediboronic acid pinacol ester, 1,8-diaminonaphthalene, protected

생성물 1

HCID 867232602-(3-(9-Ethyl-9H-imidazo[4,5-c]pyridazin-6-yl)phenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine수율 83.6%

시약·촉매·용매 3

HCID 178454861HCID 178454861, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A room temperature solution of 2-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-2,3-dihydro-1H-1,3-diaza-2-boraphenalene (Preparation 61, 7.8 g, 21.1 mmol), 4-chloro-7-ethyl-7H-imidazo[4,5-c]pyridazine (Preparation 8, 2.6 g, 14.1 mmol) and cesium carbonate (13.8 g, 42.3 mmol) in dioxane (160 mL) and water (13 mL) was degassed. 1,1′-bis(di-tert-butylphosphino) ferrocene palladium dichloride (0.91 g, 1.4 mmol) was then added in one portion and the reaction mixture was again purged with nitrogen gas three times. The resultant solution was then stirred at reflux for 16 hours. The reaction mixture was cooled to room temperature then filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with CH2Cl2:MeOH, 50:1 to afford the title compound as a yellow solid in 83.6% yield.

후처리

  1. customthe reaction mixture was again purged with nitrogen gas three times
  2. temperatureat reflux for 16 hours
  3. filtrationthen filtered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with CH2Cl2

출처 및 근거

ORD 기록
ord-f532a37def11463fbca486b17840befe
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952008B2

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