Lawesson's reagent → 5-Bromo-1-(2,6-difluorophenyl)-7-methyl-1H-pyrazolo[3,4-b]pyridine-6(7H)-thione

HRID 2261264Notes

Reaction equation

COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[Br:23][C:24]1[C:29](=O)[N:28]([CH3:31])[C:27]2[N:32]([C:35]3[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=3[F:42])[N:33]=[CH:34][C:26]=2[CH:25]=1>C1(C)C=CC=CC=1>[Br:23][C:24]1[C:29](=[S:10])[N:28]([CH3:31])[C:27]2[N:32]([C:35]3[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=3[F:42])[N:33]=[CH:34][C:26]=2[CH:25]=1

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of Lawesson's reagent (297 mg, 0.73 mmol) and 5-bromo-1-(2,6-difluorophenyl)-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (125 mg, 0.68 mmol) in toluene (8 mL) was heated to 125° C. for 15 h. The solvent was removed under reduced pressure (rotary evaporator) and the crude residue was purified on the ISCO 40 g column (5-40% EtOAc in hexanes) affording the title compound (101.6 mg) as a bright yellow crystalline solid. MS (ESI, pos.ion) m/z: 355.9/357.9 (M+1).

Workup

customThe solvent was removed under reduced pressure (rotary evaporator)
customthe crude residue was purified on the ISCO 40 g column (5-40% EtOAc in hexanes)

Sources & evidence

ORD record: ord-50bbcfbe510148b68f13b4856ba26c7a
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846944B2

Reaction notes

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