Borane → 7-Chloro-2,3-dihydrofuro[2,3-c]pyridin-3-amine

HRID 1508214Notes

Reaction equation

HRID 1508214 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]=12

Participants

4

Reactant 2

HCID 6331BoraneHCID 867219137-chlorofuro[2,3-c]pyridin-3(2H)-one O-methyl oxime

Product 1

HCID 867219147-Chloro-2,3-dihydrofuro[2,3-c]pyridin-3-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. customAt RT, the reaction mixture was quenched with sat. aq. NaHCO3 solution
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5db5633f1ef14c9ab8a1e7328cc4e178
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

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