tert-Butanol → tert-Butyl N-[8-bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]carbamate

HRID 500997Notes

Reaction equation

[Br:1][C:2]1[C:3]2[N:4]([C:9](C(O)=O)=[C:10]([S:12][CH3:13])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])C=CC=CC=1.C([N:36]([CH2:39]C)CC)C.[C:41]([OH:45])([CH3:44])([CH3:43])[CH3:42]>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]2[N:4]([C:9]([NH:36][C:39](=[O:24])[O:45][C:41]([CH3:44])([CH3:43])[CH3:42])=[C:10]([S:12][CH3:13])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

8-Bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridine-3-carboxylic acid (500 mg) was dissolved in a mixture of tert-butyl alcohol (15 mL) and toluene (50 mL), then diphenylphosphorylazide (500 mg) and triethylamine (206 mg) were added thereto. After the mixture was heated at 70° C. for 2 hours, it was stirred for 2 hours by heating under reflux. After cooled to room temperature, the reaction mixture was evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:9) to give tert-butyl N-[8-bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]carbamate (0.85 g) as a white powder.

Workup

temperatureby heating
temperatureunder reflux
temperatureAfter cooled to room temperature
customthe reaction mixture was evaporated
customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:9)

Sources & evidence

ORD record: ord-3dd437eeb54b49139a20b872c1c35aa0
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772249B2

Reaction notes

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