Potassium Carbonate → (S)-6-chloro-N-(1-(4-fluorophenyl)ethyl)-3-nitropyridin-2-amine

HRID 2189882Notes

Reaction equation

HRID 2189882 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+].[F:18][C:19]1[CH:24]=[CH:23][C:22]([C@@H:25]([NH2:27])[CH3:26])=[CH:21][CH:20]=1>CC#N>[Cl:11][C:4]1[N:3]=[C:2]([NH:27][C@H:25]([C:22]2[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=2)[CH3:26])[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 2779063(S)-1-(4-Fluorophenyl)-ethylamine

Product 1

HCID 86620612(S)-6-chloro-N-(1-(4-fluorophenyl)ethyl)-3-nitropyridin-2-amineYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of 2,6-dichloro-3-nitropyridine (2.26 g, 10.8 mmol) and potassium carbonate (1.29 g, 9.34 mmol) in anhydrous CH3CN (20 ml), was added (S)-1-(4-fluoro-phenyl)-ethylamine (1.00 g, 7.19 mmol) dropwise at 0° C. The reaction mixture was stirred at 25° C. for 17 hrs. The solid was removed by filtration and the resulted cake was washed with EtOAc (20 ml). The combined filtrate was concentrated and purified by column chromatography (hexane-EtOAc=10:1) to give the title compound as a yellow solid (1.74 g, 82%). 1H NMR (400 MHz) δ 8.65 (d, J=7.6 Hz, 1H), 8.43 (d, J=8.4 Hz, 1H), 7.51 (m, 2H), 7.16 (m, 2H), 6.81 (d, J=8.8 Hz, 1H), 5.37 (m, 1H), 1.59 (d, J=6.8 Hz, 3H).

Workup

  1. customThe solid was removed by filtration
  2. washthe resulted cake was washed with EtOAc (20 ml)
  3. concentrationThe combined filtrate was concentrated
  4. custompurified by column chromatography (hexane-EtOAc=10:1)

Sources & evidence

ORD record
ord-a939139fb1d14febbe954f506e8c1fca
Source dataset
uspto-grants-2012_12
Patent number
US08324252B2

Reaction notes

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