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

HRID 2361066

반응식

HRID 2361066 반응식
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

참가 물질

4

반응물 3

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

생성물 1

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

반응 조건

온도
130 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f5670021cc254d25b310391fb240d536
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08686155B2

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