Iodine chloride → 3-(2-Fluoro-4-iodo-phenylamino)-5-formylaminomethyl-pyrazine-2-carboxylic acid methyl ester

HRID 2064010Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Si](C)(C)C)=[CH:14][C:13]=2[F:22])=[N:9][C:8]([CH2:23][NH:24][CH:25]=[O:26])=[CH:7][N:6]=1)=[O:4].[I:27]Cl>ClCCl>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([I:27])=[CH:14][C:13]=2[F:22])=[N:9][C:8]([CH2:23][NH:24][CH:25]=[O:26])=[CH:7][N:6]=1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold (0° C.) solution of 3-(2-fluoro-4-trimethylsilanyl-phenylamino)-5-formylaminomethyl-pyrazine-2-carboxylic acid methyl ester (480 mg, 1.28 mmol) in dichloromethane (13 mL) under N2 was added dropwise a solution of 1M iodine monochloride in dichloromethane (3.0 mL, 3.0 mmol, 2.4 eq), and the mixture was stirred at 0° C. for 1.5 hour. The reaction was quenched by addition of a saturated aqueous solution of sodium thiosulfate (˜3 mL). After stirring for 10 minutes the reaction mixture was poured into ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water and brine, dried (Na2SO4), filtered and evaporated in vacuo to afford the desired product as a yellow solid (548 mg, 99%). LCMS (method C): RT=2.65 min, [M+H]+=431.

Workup

customThe reaction was quenched by addition of a saturated aqueous solution of sodium thiosulfate (˜3 mL)
stirringAfter stirring for 10 minutes the reaction mixture
additionwas poured into ethyl acetate
washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water and brine
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated in vacuo

Sources & evidence

ORD record: ord-0191e43e7e694c558f14ed6c53b9fad2
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288408B2

Reaction notes

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