Sodium Iodide → Methyl 4-amino-5-fluoro-6-(4-iodophenyl)-3-vinylpicolinate

HRID 516578Notes

Reaction equation

[B-](F)(F)(F)F.N#[O+].[NH2:8][C:9]1[C:14]([F:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19](N)=[CH:18][CH:17]=2)[N:12]=[C:11]([C:23]([O:25][CH3:26])=[O:24])[C:10]=1[CH:27]=[CH2:28].[I-:29].[Na+].S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.O.CC#N>[NH2:8][C:9]1[C:14]([F:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([I:29])=[CH:18][CH:17]=2)[N:12]=[C:11]([C:23]([O:25][CH3:26])=[O:24])[C:10]=1[CH:27]=[CH2:28]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. suspension of nitrosyl tetrafluoroborate (0.041 g, 0.348 mmol) in CH2Cl2 (1 mL) was added a solution of methyl 4-amino-6-(4-aminophenyl)-5-fluoro-3-vinylpicolinate (0.1 g, 0.348 mmol) in a 1:1 mixture of CH2Cl2 and CH3CN (4 mL). The reaction mixture was stirred at 0° C. for 30 min, then a solution of sodium iodide (0.261 g, 1.740 mmol) dissolved in a minimum of water was added and the reaction was stirred at 20° C. for 30 min. The mixture was then poured into a 10% aqueous solution of sodium sulfite and extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (SiO2, hexanes/EtOAc gradient) followed by preparative reverse phase HPLC (water/acetonitrile gradient) to afford the title compound as a white solid (32 mg, 0.080 mmol, 23.09%).

Workup

additionwas added
stirringthe reaction was stirred at 20° C. for 30 min
extractionextracted with EtOAc (3×)
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by flash column chromatography (SiO2, hexanes/EtOAc gradient)

Sources & evidence

ORD record: ord-26343ad24d7149b1a11f8013d2f730df
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09113629B2

Reaction notes

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