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

HRID 500997
Notes
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Reaction equation

HRID 500997 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 220243538-Bromo-6-methyl-2-(methylthio)imidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 22024623tert-Butyl N-[8-bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]carbamate

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

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

  1. temperatureby heating
  2. temperatureunder reflux
  3. temperatureAfter cooled to room temperature
  4. customthe reaction mixture was evaporated
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes