Isobutyl iodide → 7-bromo-8-iodo-2-isobutyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

HRID 2101354Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8](=[O:11])[NH:9][N:10]=[C:4]2[C:3]=1[I:12].C([O-])([O-])=O.[K+].[K+].I[CH2:20][CH:21]([CH3:23])[CH3:22]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8](=[O:11])[N:9]([CH2:20][CH:21]([CH3:23])[CH3:22])[N:10]=[C:4]2[C:3]=1[I:12]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirring solution of 7-bromo-8-iodo-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (2.0 g, 5.9 mmol) in 20 mL DMF at 20° C. was added K2CO3 (1.6 g, 11.8 mmol), followed by addition of 1-iodo-2-methylpropane (2.2 g, 11.8 mmol). The resulting reaction mixture was stirred at 80° C. for 3 h. Analysis by HPLC/MS indicated that starting material had been entirely consumed. The reaction mixture was brought to room temperature, diluted with water, and extracted with diethyl ether and EtOAc. The combined organic extract was washed with saturated aqueous NaHCO3 solution, then brine, then dried (MgSO4), filtered, and concentrated under reduced pressure to obtain the title compound (2.1 g, 5.3 mmol) as a light tan solid. MS: [M+H]+=396. 1H NMR (CDCl3): δ 7.65 (d, J=1.9 Hz, 1H), 6.68 (d, J=1.8 Hz, 1H), 3.82 (d, J=1.8, 2H), 2.33-2.30 (m, 1H), 0.96 (d, J=1.7 Hz, 6H).

Workup

customThe resulting reaction mixture
customhad been entirely consumed
customwas brought to room temperature
additiondiluted with water
extractionextracted with diethyl ether and EtOAc
extractionThe combined organic extract
washwas washed with saturated aqueous NaHCO3 solution
dry with materialbrine, then dried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-e75bebc8746a44828b9207c203c73673
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572808B2

Reaction notes

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