Iodine chloride → HCID 67079829, compound

HRID 453396Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([Si](C)(C)C)=[CH:17][C:16]=1[F:25])[C:10](=[O:26])[NH:9][CH2:8]2)=[O:4].[I:27]Cl>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([I:27])=[CH:17][C:16]=1[F:25])[C:10](=[O:26])[NH:9][CH2:8]2)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-(2-fluoro-4-trimethylsilanyl-phenylamino)-1-oxo-2,3-dihydro-1H-isoindole-5-carboxylic acid methyl ester (284 mg, 0.76 mmol) in DCM (5 ml) at 0° C. was added a solution of iodine monochloride (246 mg, 1.52 mmol) in DCM (1.5 mL). The reaction mixture was stirred at 0° C. for 4 hours. The reaction was quenched by the addition of water (10 mL) then diluted with saturated aqueous sodium thiosulfate solution (10 mL). The resultant mixture was extracted with ethyl acetate (3×20 mL). The combined organic fractions were washed with brine (20 mL), dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0-7% methanol in DCM) to yield the title compound as a brown solid (220 mg, 68%). LCMS (Method B): RT=3.65 min, 2M+H+=853.

Workup

customThe reaction was quenched by the addition of water (10 mL)
additionthen diluted with saturated aqueous sodium thiosulfate solution (10 mL)
extractionThe resultant mixture was extracted with ethyl acetate (3×20 mL)
washThe combined organic fractions were washed with brine (20 mL)
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5065e43c69ec4d06a6deba5a34e70710
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492427B2

Reaction notes

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