Iodine chloride → 7-Fluoro-3-(2-fluoro-4-iodo-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester

HRID 2264937Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[NH:14][C:13]2[C:12]([F:15])=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([Si](C)(C)C)=[CH:19][C:18]=1[F:27])=[O:5])[CH3:2].[I:28]Cl>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[NH:14][C:13]2[C:12]([F:15])=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([I:28])=[CH:19][C:18]=1[F:27])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 2.5 °C

Procedure

A solution of 7-fluoro-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (500 mg, 1.28 mmol) in CH2Cl2 (15 mL) was cooled to 0-5° C. and treated dropwise with iodine monochloride solution (2.6 mL, 1M in CH2Cl2). The mixture was stirred at 0-5° C. for one hour and then quenched by addition of a saturated aqueous sodium thiosulfate solution (10 mL). The mixture was diluted with water and dichloromethane. The precipitate formed was filtered off, washed with diethyl ether and dried under vacuum at 50° C. to give the title compound as a yellow solid (218 mg, 38%). LCMS (method B): RT=2.87 min, M+H+= 444.

Workup

customquenched by addition of a saturated aqueous sodium thiosulfate solution (10 mL)
additionThe mixture was diluted with water and dichloromethane
customThe precipitate formed
filtrationwas filtered off
washwashed with diethyl ether
customdried under vacuum at 50° C.

Sources & evidence

ORD record: ord-ebe984b0cdaa4b0aa12744c3ae55bb48
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855216B2

Reaction notes

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