Borane → 5-Chloro-2,3-dihydrofuro[2,3-c]pyridin-3-amine
Reaction equation
CO[N:3]=[C:4]1[C:12]2[C:7](=[CH:8][N:9]=[C:10]([Cl:13])[CH:11]=2)[O:6][CH2:5]1.B>C1COCC1>[Cl:13][C:10]1[CH:11]=[C:12]2[CH:4]([NH2:3])[CH2:5][O:6][C:7]2=[CH:8][N:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To a solution of 5-chlorofuro[2,3-c]pyridin-3(2H)-one O-methyl oxime (0.71 mmol) in 1 mL THF were added 2.2 mL of a borane solution (1M in THF). The mixture was heated to 40° C. for 1 h in a closed vessel. At RT, the reaction mixture was quenched with MeOH, the pH was adjusted to 9 with 1M NaOH solution and the mixture was extracted with EtOAc. 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 MeOH
- extractionthe mixture was extracted with EtOAc
- dry with materialThe combined organic layers were dried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-bb23c598522c4ae1bfac30fd1e0b1249
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221832B2
Reaction notes
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