Potassium Carbonate → 3-Chloro-2-(2-fluoro-3-nitro-phenyl)-pyridine

HRID 1527526Notes

Reaction equation

Br[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[F:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:11]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.CCOC(C)=O>[Cl:8][C:7]1[C:2]([C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([N+:16]([O-:18])=[O:17])[C:10]=2[F:9])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 2-bromo-3-chloropyridine [96424-68-9] (144 mg, 0.75 mmol) and 2-fluoro-3-nitrophenylboronic acid pinacol ester [1189042-70-3] (200 mg, 0.75 mmol) in dioxane (4 mL) and water (1 mL) was added potassium carbonate (259 mg, 1.87 mmol) and Pd(dppf)Cl2CH2Cl2 adduct (61.2 mg, 0.075 mmol). The solution was heated for 60 min at 120° C. under microwave irradiation. The reaction mixture was diluted with EtOAc and the resulting solution was washed successively with saturated aqueous NaHCO3 solution and brine, then dried (Phase separator) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (c-hexane/EtOAc 4:1) to give the title compound. MS (LC-MS): 253 [M+H]+; tR (HPLC conditions k): 3.45 min.

Workup

washthe resulting solution was washed successively with saturated aqueous NaHCO3 solution and brine
customdried (Phase separator)
concentrationconcentrated under reduced pressure
customThe residue was purified by flash chromatography on silica gel (c-hexane/EtOAc 4:1)

Sources & evidence

ORD record: ord-2a584b390beb442bbca984a17adaac6f
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085555B2

Reaction notes

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