Reaction equation
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]=1Participants
4
Conditions
- Temperature
- 130 °C
Procedure
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.
Workup
- custompurged with nitrogen for several minutes
- addition1.8 mL of DMSO was added
- customthe tube was sealed
- temperatureUpon cooling the mixture
- additionwas diluted with EtOAc
- washwashed with water
- extractionThe aqueous portion was extracted with EtOAc
- dry with materialthe combined organic portions were dried with MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-af2976db121f4f9293a0fa65459d21fd
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08022221B2
Linked notes
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