Potassium Carbonate → HCID 86620611, compound

HRID 75933Notes

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

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

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

Sources & evidence

ORD record: ord-36e0e0a1539e489cb8fb1207a4e95ad1
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835465B2

Reaction notes

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