Cesium carbonate → N-(4-(3-bromopyridin-4-yloxy)phenyl)-4-phenylphthalazin-1-amine

HRID 2361066

反応式

HRID 2361066 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].Cl.[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1Cl.[C:16]1([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]([NH:32][C:33]3[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=3)=[N:24][N:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[O:39][C:36]1[CH:35]=[CH:34][C:33]([NH:32][C:25]2[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:22]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[N:23][N:24]=2)=[CH:38][CH:37]=1

参加物

4

反応物 3

HCID 10796Cesium carbonateHCID 28691684-((4-Phenylphthalazin-1-yl)amino)phenolHCID 469414223-Bromo-4-chloropyridine hydrochloride

生成物 1

HCID 66731439N-(4-(3-bromopyridin-4-yloxy)phenyl)-4-phenylphthalazin-1-amine

反応条件

温度
130 °C

実験手順

A resealable reaction tube was charged with cesium carbonate (0.873 g, 0.268 mmol), 3-bromo-4-chloropyridine hydrochloride (0.205 g, 0.894 mmol) and 4-(4-phenylphthalazin-1-ylamino)phenol (0.280 g, 0.894 mmol) and purged with nitrogen for several minutes. 1.8 mL of DMSO was added, the tube was sealed, and the reaction mixture was heated to 130° C. for 3 h. Upon cooling the mixture was diluted with EtOAc and washed with water. The aqueous portion was extracted with EtOAc, and the combined organic portions were dried with MgSO4 and concentrated. N-(4-(3-bromopyridin-4-yloxy)phenyl)-4-phenylphthalazin-1-amine was isolated as an orange solid. MS m/z=470 [M+H]+. Calc'd for C25H17BrN4O: 469.33.

後処理

  1. custompurged with nitrogen for several minutes
  2. addition1.8 mL of DMSO was added
  3. customthe tube was sealed
  4. temperatureUpon cooling the mixture
  5. additionwas diluted with EtOAc
  6. washwashed with water
  7. extractionThe aqueous portion was extracted with EtOAc
  8. dry with materialthe combined organic portions were dried with MgSO4
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-f5670021cc254d25b310391fb240d536
出典データセット
uspto-grants-2014_04
特許番号
US08686155B2

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