N-Iodosuccinimide → 3-bromo-5-(2-chloro-4-fluorophenyl)-4-iodo-1-methyl-1H-pyrazole

HRID 2276025Notes

Reaction equation

[Br:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=2[Cl:14])[N:4]([CH3:15])[N:3]=1.[I:16]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[C:6]([I:16])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=2[Cl:14])[N:4]([CH3:15])[N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 3-bromo-5-(2-chloro-4-fluorophenyl)-1-methyl-1H-pyrazole (i.e. the product of Step C) (620 mg, 2.14 mmol) in N,N-dimethylformamide (8 mL) at 60° C. was added N-iodosuccinimide (963 mg, 4.28 mmol). The reaction mixture was stirred at 60° C. for 3 h, and then diluted with ethyl acetate, washed with water and saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The material was purified by silica gel chromatography (5 to 30% gradient of ethyl acetate in hexanes as eluant) to provide the title compound as a pale yellow solid (515 mg) melting at 139-141° C.

Workup

washwashed with water and saturated aqueous sodium chloride solution
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe material was purified by silica gel chromatography (5 to 30% gradient of ethyl acetate in hexanes as eluant)

Sources & evidence

ORD record: ord-c8b3b3156cf74ee0a9b5e9537df8f7e9
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09131693B2

Reaction notes

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