Potassium Carbonate → HCID 86620611, compound

HRID 2189893Notes

Reaction equation

HRID 2189893 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH2:18][C@H:19]([C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)[CH2:20][OH:21]>C(#N)C>[Cl:11][C:4]1[N:3]=[C:2]([NH:18][C@H:19]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:20][OH:21])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 852392,6-Dichloro-3-nitropyridineHCID 10583003(R)-2-Amino-2-(4-fluorophenyl)ethanol

Product 1

HCID 86620611HCID 86620611, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of 2,6-dichloro-3-nitropyridine (0.933 g, 4.83 mmol) and potassium carbonate (0.58 g, 4.19 mmol) in anhydrous acetonitrile (10 ml) was added (R)-2-amino-2-(4-fluoro phenyl)ethanol (1.00 g, 7.19 mmol) at 0° C. The resulting reaction mixture was stirred at 25° C. for 18 hours. The solid was removed by filtration and washed with EtOAc (20 ml). After evaporation of the solvent, the resulting residue was purified by column chromatography (hexane-EtOAc=5:1) to give the title compound as a yellow solid (0.77 g, 61%). 1H NMR (400 MHz) δ 8.96 (d, J=7.6 Hz, 1H), 8.46 (d, J=8.4 Hz, 1H), 7.45 (m, 2H), 7.15 (m, 2H), 6.81 (d, J=8.8 Hz, 1H), 5.27 (m, 2H), 3.80 (m, 2H).

Workup

  1. customThe resulting reaction mixture
  2. customThe solid was removed by filtration
  3. washwashed with EtOAc (20 ml)
  4. customAfter evaporation of the solvent
  5. customthe resulting residue was purified by column chromatography (hexane-EtOAc=5:1)

Sources & evidence

ORD record
ord-a238644c8e2a4eb7aea99d70ca25eeab
Source dataset
uspto-grants-2012_12
Patent number
US08324252B2

Reaction notes

Loading…