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 1846038ノート

反応式

HRID 1846038 の反応式
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]

参加物

7

反応物 3

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

生成物 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]diazaborinine収率 83.6%

試薬・触媒・溶媒 3

HCID 178454861HCID 178454861、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f532a37def11463fbca486b17840befe
出典データセット
uspto-grants-2015_02
特許番号
US08952008B2

反応ノート

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