Benzoyl Peroxide → 1-Acetyl-3-bromomethyl-6-fluoro-1H-indazole

HRID 1956371Notes

Reaction equation

[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:13])[CH:11]=2)[C:6]([CH3:14])=[N:5]1)(=[O:3])[CH3:2].C1C(=O)N([Br:22])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:13])[CH:11]=2)[C:6]([CH2:14][Br:22])=[N:5]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

1-Acetyl-6-fluoro-3-methyl-1H-indazole (5.77 g, 33.1 mmol) in CCl4 (100 mL) was treated with NBS (3.64 g, 20 mmol) and benzoyl peroxide (0.388 g, 1.6 mmol) and the mixture was heated at 70° C. for 6 h. The mixture was concentrated and the residue quickly filtered through a plug of flash silica eluting with 2%→7% EtOAc in hexane to give the crude title compound (2.97 g, 65%) contaminated with traces of dibromide and starting material. This was conveniently used directly in subsequent reactions without further purification.

Workup

concentrationThe mixture was concentrated
filtrationthe residue quickly filtered through a plug of flash silica eluting with 2%→7% EtOAc in hexane

Sources & evidence

ORD record: ord-33b9c4ef7e20440181ed8ebe81a64e00
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05780475

Reaction notes

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