Sodium Carbonate → N-(4-(3-bromopyridin-4-yloxy)phenyl)-4-phenylphthalazin-1-amine

HRID 227798

反応式

HRID 227798 の反応式
F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[F:19][C:20]1[CH:25]=[C:24](B(O)O)[CH:23]=[CH:22][N:21]=1.[Br:29][C:30]1[CH:31]=[N:32][CH:33]=[CH:34][C:35]=1[O:36][C:37]1[CH:42]=[CH:41][C:40]([NH:43][C:44]2[C:53]3[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=3)[C:47]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)=[N:46][N:45]=2)=[CH:39][CH:38]=1.C(=O)([O-])[O-].[Na+].[Na+]>CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[F:19][C:20]1[CH:25]=[C:24]([C:34]2[CH:33]=[N:32][CH:31]=[CH:30][C:35]=2[O:36][C:37]2[CH:38]=[CH:39][C:40]([NH:43][C:44]3[C:53]4[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=4)[C:47]([C:54]4[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=4)=[N:46][N:45]=3)=[CH:41][CH:42]=2)[CH:23]=[CH:22][N:21]=1.[Br:29][C:30]1[CH:31]=[N:32][CH:33]=[CH:34][C:35]=1[O:36][C:37]1[CH:42]=[CH:41][C:40]([NH:43][C:44]2[C:53]3[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=3)[C:47]([C:54]3[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=3)=[N:46][N:45]=2)=[CH:39][CH:38]=1

参加物

9

反応物 4

HCID 10340Sodium CarbonateHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 27833962-Fluoropyridine-4-boronic acidHCID 66731439N-(4-(3-bromopyridin-4-yloxy)phenyl)-4-phenylphthalazin-1-amine

生成物 2

HCID 66731439N-(4-(3-bromopyridin-4-yloxy)phenyl)-4-phenylphthalazin-1-amineHCID 66732281N-(4-(3-(2-fluoropyridin-4-yl)pyridin-4-yloxy)phenyl)-4-phenylphthalazin-1-amine

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A resealable reaction tube was charged with tri-tert-butylphosphonium tetrafluoroborate (0.024 g, 0.082 mmol), palladium (II) acetate (0.009 g, 0.041 mmol), 2-fluoropyridine4-boronic acid (0.086 g, 0.614 mmol) and N-(4-(3-bromopyridin4-yloxy)phenyl)-4-phenylphthalazin-1-amine (0.192 mg, 0.409 mmol) and was purged with nitrogen for several minutes. 1.2 mL of dioxane and 2.0 M aqueous sodium carbonate (0.614 mL, 0.123 mmol) were added, the tube was sealed, and the reaction mixture was heated to 100° C. for 48 h. The mixture was diluted with EtOAc and washed with water. The organic portion was dried with MgSO4 and concentrated. Purification by Gilson reverse phase liquid chromatography (5-70% ACN/water/0.1% TFA over 14 min) provided N-(4-(3-(2-fluoropyridin-4-yl)pyridin-4-yloxy)phenyl)-4-phenylphthalazin-1-amine as a mixture with the hydrodehalogenation product of N-(4-(3-bromopyridin-4-yloxy)phenyl)4-phenylphthalazin-1-amine.

後処理

  1. customwas purged with nitrogen for several minutes
  2. customthe tube was sealed
  3. washwashed with water
  4. dry with materialThe organic portion was dried with MgSO4
  5. concentrationconcentrated
  6. customPurification by Gilson reverse phase liquid chromatography (5-70% ACN/water/0.1% TFA over 14 min)

出典と根拠

ORDレコード
ord-bfaff0fbea714597b399ff08fb409554
出典データセット
uspto-grants-2009_07
特許番号
US07560551B2

関連ノート

読み込み中…