Water → 4-Methylsulfanyl-2'-nitro-biphenyl-2-ylamine
Reaction equation
CO.[O:3]1CCOCC1.I[C:10]1[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][C:11]=1[N+:18]([O-])=O.CCN(CC)CC.[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1B(O)O.[OH2:38]>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:17][S:16][C:13]1[CH:14]=[CH:15][C:10]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N+:28]([O-:3])=[O:38])=[C:11]([NH2:18])[CH:12]=1Participants
7
Conditions
- Temperature
- 70 °C
Procedure
A methanol/dioxane (20 mL/5 mL of methanol/dioxane) solution/suspension of 4-iodo-3-nitrothioanisole (1 mmol), Pd(OAc)2 (0.01 mmol) was purged with argon for ˜5 min. To this solution Et3N (3 mmol), and 5 mL of water were added and purged with argon for another 5 min. To the above solution, 2-aminophenyl boronic acid (2 mmol, solution in 5 mL of DMF, purged with argon), was added and the reaction mixture was heated at 70° C. (oil bath temperature) for 2 h. The reaction was monitored by HPLC and LC-MS to follow the product formation. The reaction mixture was then cooled down to room temperature and filtered through diatomaceous earth. The filtrate was concentrated and purified using preparative HPLC.
Workup
- customwas purged with argon for ˜5 min
- custompurged with argon for another 5 min
- temperatureThe reaction mixture was then cooled down to room temperature
- filtrationfiltered through diatomaceous earth
- concentrationThe filtrate was concentrated
- custompurified
Sources & evidence
- ORD record
- ord-a02241a396b04110aadf7100cbfaca84
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07405235B2
Reaction notes
Loading…