Iodine chloride → 7-(2-Fluoro-4-iodo-phenylamino)-6-methyl-8-nitro-2,3-dihydro-oxazolo[3,2-a]pyridin-5-one

HRID 1259385Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([Si](C)(C)C)[CH:5]=[CH:4][C:3]=1[NH:12][C:13]1[C:14]([N+:24]([O-:26])=[O:25])=[C:15]2[O:23][CH2:22][CH2:21][N:16]2[C:17](=[O:20])[C:18]=1[CH3:19].[I:27]Cl>C(Cl)Cl.F[B-](F)(F)F.[Ag+]>[F:1][C:2]1[CH:7]=[C:6]([I:27])[CH:5]=[CH:4][C:3]=1[NH:12][C:13]1[C:14]([N+:24]([O-:26])=[O:25])=[C:15]2[O:23][CH2:22][CH2:21][N:16]2[C:17](=[O:20])[C:18]=1[CH3:19]

Participants

Conditions

Temperature: -50 °C

Procedure

A stirred solution of 7-(2-fluoro-4-trimethylsilanyl-phenylamino)-6-methyl-8-nitro-2,3-dihydro-oxazolo[3,2-a]pyridin-5-one (0.25 g, 0.66 mmol) in dry DCM (10 mL) and iodine monochloride (0.8 mL) were added to silver tetrafluoroborate (0.4 g, 2.05 mmol) in DCM (10 mL) previously degassed with nitrogen for 30 minutes at −50° C. The resulting mixture was stirred at −50° C. for 1 hour. The reaction was monitored by TLC (50% ethylacetate in hexane). This was followed by the addition of 20 mL of sodium thiosulphate and filtered through celite. The filtrate was concentrated to afford 0.2 g of the product (70% yield).

Workup

custompreviously degassed with nitrogen for 30 minutes at −50° C
additionThis was followed by the addition of 20 mL of sodium thiosulphate
filtrationfiltered through celite
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-a89540fe450a4a5ca9757112bbeb757a
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466289B2

Reaction notes

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