N-Iodosuccinimide → 2,3-Dichloro-4-iodofuro[2,3-c]pyridin-7-amine
Reaction equation
[Cl:1][C:2]1[O:11][C:5]2=[C:6]([NH2:10])[N:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[Cl:12].[I:13]N1C(=O)CCC1=O>CC#N>[Cl:1][C:2]1[O:11][C:5]2=[C:6]([NH2:10])[N:7]=[CH:8][C:9]([I:13])=[C:4]2[C:3]=1[Cl:12]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A solution of 2,3-dichlorofuro[2,3-c]pyridin-7-amine (5.7 g, 28.2 mmol) in MeCN (200 mL) was treated with N-iodosuccinimide (9.57 g, 42.3 mmol), added portionwise over 5-10 min. The mixture was heated at 60° C. for 16 h. After cooling to RT, the reaction was quenched with 20% aqueous sodium thiosulfate and stirred for 10 min. EtOAc (200 mL) was added and the phases separated. The organic phase was washed with 20% aqueous sodium thiosulfate (50 mL), then water (2×100 mL) and finally with brine. After drying over Na2SO4, the organic extracts were filtered and concentrated in vacuo. The material was purified using flash chromatography eluting with 2% MeOH in DCM to afford 3.8 g (41%) of the title compound. 1H NMR (300 MHz, DMSO-d6): δ 6.75 (br. s, 2H); 8.02 (s, 1H).
Workup
- additionadded portionwise over 5-10 min
- temperatureAfter cooling to RT
- customthe reaction was quenched with 20% aqueous sodium thiosulfate
- additionEtOAc (200 mL) was added
- customthe phases separated
- washThe organic phase was washed with 20% aqueous sodium thiosulfate (50 mL)
- dry with materialAfter drying over Na2SO4
- filtrationthe organic extracts were filtered
- concentrationconcentrated in vacuo
- customThe material was purified
- washeluting with 2% MeOH in DCM
Sources & evidence
- ORD record
- ord-442ddd1d72184d4581e9cc5653ee5715
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08378104B2
Reaction notes
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