Iodine chloride → 4-(2-Fluoro-4-iodo-phenylamino)-benzo[d]isothiazole-5-carboxylic acid tert-butyl ester

HRID 79029Notes

Reaction equation

[C:1]([O:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]2[S:15][N:14]=[CH:13][C:12]=2[C:16]=1[NH:17][C:18]1[CH:23]=[CH:22][C:21]([Si](C)(C)C)=[CH:20][C:19]=1[F:28])=[O:7])([CH3:4])([CH3:3])[CH3:2].[I:29]Cl>C(Cl)Cl.S([O-])([O-])(=O)=S.[Na+].[Na+]>[C:1]([O:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]2[S:15][N:14]=[CH:13][C:12]=2[C:16]=1[NH:17][C:18]1[CH:23]=[CH:22][C:21]([I:29])=[CH:20][C:19]=1[F:28])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution 4-(2-fluoro-4-trimethylsilanyl-phenylamino)-benzo[d]isothiazole-5-carboxylic acid tert-butyl ester (416 mg, 1.0 mmol) in DCM (10 mL) at −78° C. was added iodine monochloride as a solution in DCM (2.0 mL, 1M, 2.0 mmol). The reaction mixture was stirred at −78° C. for 1 hour then diluted with saturated aqueous sodium thiosulfate solution and extracted with DCM. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo to yield the title compound as a yellow foam (459 mg, 98%). LCMS (Method B): RT=5.32 min, [M+H]+=471.

Workup

extractionextracted with DCM
washThe combined organic extracts were washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2ff70ac5481048b68eb181435c44d288
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841462B2

Reaction notes

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