Iodine chloride → 5-Fluoro-2-(2-fluoro-4-iodo-phenylamino)-6-formylaminomethyl-nicotinic acid methyl ester

HRID 2076182Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([CH2:11][NH:12][CH:13]=[O:14])=[N:6][C:5]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([Si](C)(C)C)=[CH:18][C:17]=1[F:26].[I:28]Cl>ClCCl>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([CH2:11][NH:12][CH:13]=[O:14])=[N:6][C:5]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([I:28])=[CH:18][C:17]=1[F:26]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-fluoro-2-(2-fluoro-4-trimethylsilanyl-phenylamino)-6-formylaminomethyl-nicotinic acid methyl ester (2.4 g, 6.1 mmol) in dichloromethane (15 mL) at 0° C. was added ICl (2.0 g, 12.2 mmol). The mixture was stirred at 0° C. for 0.5 hour, then quenched with water, washed with a saturated solution of sodium sulphite followed by brine, dried (Na2SO4), filtered and evaporated in vacuo to afford the title compound as a brown solid (2.7 g, 98%). LCMS (method B): RT=3.81 min, [M+H]+=448.

Workup

customquenched with water
washwashed with a saturated solution of sodium sulphite
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated in vacuo

Sources & evidence

ORD record: ord-b370a002f30440c6834184c9f1f2fef3
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923456B2

Reaction notes

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