Iodine → 7-Chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-c]pyridine
Reaction equation
CO[C:3](=O)[NH:4][C:5]1[C:6]([Cl:16])=[N:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][C:10]=1I.[CH:18]([Li])(CC)C.COC(=O)NC1C(Cl)=NC(C(F)(F)F)=CC=1.CN(C)CCN(C)C.II>C1COCC1>[Cl:16][C:6]1[N:7]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:10]2[CH:18]=[CH:3][NH:4][C:5]=12Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
(2-Chloro-4-iodo-6-trifluoromethyl-pyridin-3-yl)-carbamic acid methyl ester: sec-Butyllithium solution (1.3 M in cyclohexane, 7.55 mL, 5.81 mmol) was added at −78° C. to a solution of (2-chloro-6-trifluoromethyl-pyridin-3-yl)-carbamic acid methyl ester (1.00 g, 3.93 mmol) and N,N,N′,N′-tetramethylethylenediamine (1.14 g, 9.82 mmol) in THF (50 mL). The solution was stirred for 1 h at −10° C., then cooled again to −78° C. and treated with a solution of iodine (1.66 g, 6.52 mmol) in THF (20 mL). After stirring for 1 h at −10° C., the reaction mixture was partitioned between ethyl acetate and 30% aq. sodium sulfite solution. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography of the residue (SiO2, dichloromethane) afforded the title compound (810 mg, 54%). White solid, MS (EI) 345.0 (100), 379.9 (2, M+).
Workup
- temperaturecooled again to −78° C.
- stirringAfter stirring for 1 h at −10° C.
- customthe reaction mixture was partitioned between ethyl acetate and 30% aq. sodium sulfite solution
- washThe organic layer was washed with brine
- dry with materialdried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-0c45dbaa8b0c4c4ca797d20c7dadcb06
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691876B2
Reaction notes
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