Triphenylphosphine → 3-(4-Pyridyl)-2-(4-fluorophenyl)indole
Reaction equation
I[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])(=O)C.[K+].[N:33]1[CH:38]=[CH:37][C:36]([C:39]#[C:40][C:41]2[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=2)=[CH:35][CH:34]=1>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CN(C=O)C>[N:33]1[CH:38]=[CH:37][C:36]([C:39]2[C:2]3[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=3)[NH:4][C:40]=2[C:41]2[CH:42]=[CH:43][C:44]([F:47])=[CH:45][CH:46]=2)=[CH:35][CH:34]=1Participants
9
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 100 °C
Procedure
2-Iodoaniline (2) (525 mg, 2.40 mmol) was added to palladium acetate (26.9 mg, 0.120 mmol), triphenyl phosphine (31.5 mg, 0.120 mmol), potassium acetate (1.18 g, 12.0 mmol), tetrabutylammonium chloride (547 20 mg, 2.40 mmol), 1-(4-pyridyl)-2-(4-fluorophenyl)ethyne (1) (1.0 g, 4.8 mmol), and DMF (20 mL). The reaction was warmed to 100° C. for 17 h under argon. After cooling to 23° C., the reaction was poured into water (200 mL), extracted with ethyl acetate (3×100 mL), and dried (MgSO4). After concentration in vacuo, the residue was purified by flash chromatography on silica gel (methanol:ethyl acetate 1:19) to afford indoles (3) and (4) as a mixture of regioisomers (4:1): Mass Spectrum (CI) 289 (MH+).
Workup
- temperatureAfter cooling to 23° C.
- extractionextracted with ethyl acetate (3×100 mL)
- dry with materialdried (MgSO4)
- concentrationAfter concentration in vacuo
- customthe residue was purified by flash chromatography on silica gel (methanol:ethyl acetate 1:19)
Sources & evidence
- ORD record
- ord-78f53c63766c44ba8960fd62c1edef21
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06180643B2
Reaction notes
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