2-Fluoro-4-iodoaniline → HCID 57636896, compound

HRID 1186760Notes

Reaction equation

[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl[C:21]1[N:22]([CH3:33])[C:23](=[O:32])[C:24]([CH3:31])=[CH:25][C:26]=1[C:27]([O:29][CH3:30])=[O:28]>C1COCC1>[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:21]1[N:22]([CH3:33])[C:23](=[O:32])[C:24]([CH3:31])=[CH:25][C:26]=1[C:27]([O:29][CH3:30])=[O:28]

Participants

Conditions

Temperature: -78 °C

Procedure

An oven dried three-necked flask was charged with 2-fluoro-4-iodoaniline (2.08 g, 8.79 mmol) and dry THF (40 mL). The mixture was cooled at −78° C. and LiHMDS (17.79 mL, 1.0 M, THF) was added dropwise. The reaction was stirred an additional hour at this temperature and methyl 2-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylate (1.89 g, 8.79 mmol) previously dissolved in dry THF (30 mL) was added. The mixture was slowly warmed to room temperature and stirred an additional 2 hours and quenched with 2N aq. HCl. The resulting mixture was further diluted with EtOAc and the organic layer was washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The brown residue was purified by flash chromatography (Biotage system) using a gradient of EtOAc (0-25%) in hexane to afford the title product (2.9 g, 79%).

Workup

additionwas added
temperatureThe mixture was slowly warmed to room temperature
customquenched with 2N aq. HCl
additionThe resulting mixture was further diluted with EtOAc
washthe organic layer was washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure
customThe brown residue was purified by flash chromatography (Biotage system)

Sources & evidence

ORD record: ord-03ae1c5441b943d39f9ca6f6cc95b69d
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673919B2

Reaction notes

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