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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
ノート
印刷プレビュー

反応式

HRID 500997 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140
Toluene
溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3dd437eeb54b49139a20b872c1c35aa0
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07772249B2

反応ノート

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