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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
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HRID 500997 반응식
[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
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140
Toluene
용매

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온도
70 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3dd437eeb54b49139a20b872c1c35aa0
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07772249B2

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