Borane → 7-Chloro-2,3-dihydrofuro[2,3-c]pyridin-3-amine
Reaction equation
CO[N:3]=[C:4]1[C:12]2[C:7](=[C:8]([Cl:13])[N:9]=[CH:10][CH:11]=2)[O:6][CH2:5]1.B>C1COCC1>[Cl:13][C:8]1[N:9]=[CH:10][CH:11]=[C:12]2[CH:4]([NH2:3])[CH2:5][O:6][C:7]=12Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 7-chlorofuro[2,3-c]pyridin-3(2H)-one O-methyl oxime (0.045 mmol) in 1 mL THF were added 10 mL of a borane solution (1M solution in THF). The mixture was heated to 60° C. overnight in a closed vessel. At RT, the reaction mixture was quenched with sat. aq. NaHCO3 solution and extracted with EtOAc (3×). The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the desired product as yellow oil;
Workup
- customAt RT, the reaction mixture was quenched with sat. aq. NaHCO3 solution
- extractionextracted with EtOAc (3×)
- dry with materialThe combined organic layers were dried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-5db5633f1ef14c9ab8a1e7328cc4e178
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221832B2
Reaction notes
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