Aniline → Phenyl-(6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3',4'-d]pyrrol-4-yl)-amine
Reaction equation
Cl[C:2]1[C:10]2[C:9]3[CH2:11][NH:12][CH2:13][CH2:14][C:8]=3[NH:7][C:6]=2[N:5]=[CH:4][CH:3]=1.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[OH-].[K+]>C(O)(C)(C)C.CCOC(C)=O.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:16]1([NH:15][C:2]2[C:10]3[C:9]4[CH2:11][NH:12][CH2:13][CH2:14][C:8]=4[NH:7][C:6]=3[N:5]=[CH:4][CH:3]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
4-Chloro-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrole (100 mg, 0.48 mmol), aniline (0.13 mL, 1.44 mmol), Pd(OAc)2 (5 mg, 0.02 mmol), X-Phos (23 mg, 0.05 mmol), and KOH (162 mg, 2.89 mmol) were dissolved in tert-butanol (2.0 mL), and stirred overnight at 100° C. The reaction mixture diluted with EtOAc/H2O, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude material was triturated with EtOAc, filtered, washed with EtOAc, and dried under vacuum to provide 3 (63 mg, 50% yield) as a tan solid. LC-MS (M+H=265, obsd.=265).
Workup
- filtrationfiltered through an Extrelut column
- washThe column was washed with EtOAc
- concentrationthe filtrate was concentrated
- customThe crude material was triturated with EtOAc
- filtrationfiltered
- washwashed with EtOAc
- customdried under vacuum
Sources & evidence
- ORD record
- ord-b228d06ace434a899ba0d464bc3d9bdc
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853391B2
Reaction notes
Loading…