Acridan → N-[4-(Benzothiazol-2-yl)-Phenyl]Acridan
Reaction equation
[CH:1]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.CC(C)([O-])C.[Na+].Br[C:35]1[CH:40]=[CH:39][C:38]([C:41]2[S:42][C:43]3[CH:49]=[CH:48][CH:47]=[CH:46][C:44]=3[N:45]=2)=[CH:37][CH:36]=1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[S:42]1[C:43]2[CH:49]=[CH:48][CH:47]=[CH:46][C:44]=2[N:45]=[C:41]1[C:38]1[CH:39]=[CH:40][C:35]([N:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:13][C:14]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=3)=[CH:36][CH:37]=1Participants
7
Procedure
A mixture of 3.74 g of acridan (20 mmol), 69 mg of Pd(OAc)2 (0.3 mmol), 44 mg of tri-t-butylphosphine (0.22 mmol), 2.88 g of sodium t-butoxide (30 mmol), and 6.0 g of 2-(4-bromophenyl)benzothiazole (20 mmol) in 60 mL of toluene was stirred at room temperature for 1 h under inert atmosphere, followed by heating at 50° C. for 1 h. The reaction mixture was cooled to room temperature, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography with 15% ethyl acetate in hexanes. NMR analysis confirmed that 3.1 g of the N-arylated acridan product was isolated.
Workup
- temperatureby heating at 50° C. for 1 h
- temperatureThe reaction mixture was cooled to room temperature
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by column chromatography with 15% ethyl acetate in hexanes
- customwas isolated
Sources & evidence
- ORD record
- ord-f11c4018188149389bde5934550c33e3
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06410732B2
Reaction notes
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