2-(Dicyclohexylphosphino)biphenyl → 2-(6-Aminopyridin-3-yl)propan-2-ol

HRID 2069733Notes

Reaction equation

HRID 2069733 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[Li][N:38]([Si](C)(C)C)[Si](C)(C)C>CCOC(C)=O.Cl>[NH2:38][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 27342162-(Dicyclohexylphosphino)biphenylHCID 125621182-(6-Chloropyridin-3-yl)propan-2-olHCID 178418261HCID 178418261, compound

Product 1

HCID 594737712-(6-Aminopyridin-3-yl)propan-2-olYield 95.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

In a flame-dried seal tube reaction vial, under argon atmosphere, add 2-(6-Chloro-pyridin-3-yl)-propan-2-ol (750 mg, 4.375 mmol), 2-(dicyclohexylphosphino)-biphenyl (307 mg, 0.875 mmol) and then add LiN(TMS)2 (1M in THF, 13.5 mL, 13.5 mmol). Seal the tube and heat it up to 90° C. for 18 hours. The dark reaction mixture was then diluted with EtOAc (10 mL). HCl (2M) (10 drops) was added with stirring. The reaction mixture was then concentrated and loaded onto ISCO separation column and eluted with 5% MeOH/(1/1 EtOAC/Hex) to afford 2-(6-Amino-pyridin-3-yl)-propan-2-ol as solid (635 mg, yield 95%).

Workup

  1. customIn a flame-dried seal tube
  2. customreaction vial
  3. customSeal the tube
  4. customThe dark reaction mixture
  5. concentrationThe reaction mixture was then concentrated
  6. customloaded onto ISCO separation column
  7. washeluted with 5% MeOH/(1/1 EtOAC/Hex)

Sources & evidence

ORD record
ord-cb20349881654a9293cce4a13ca3e69c
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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