Borane → 5-Chloro-2,3-dihydrofuro[2,3-c]pyridin-3-amine

HRID 1508220Notes

Reaction equation

HRID 1508220 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]=1

Participants

4

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

  1. customAt RT, the reaction mixture was quenched with MeOH
  2. extractionthe mixture was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb23c598522c4ae1bfac30fd1e0b1249
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

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