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tert-Butanol → (6-Bromo-2-phenyl-imidazo[1,2-a]pyridin-7-yl)-carbamic acid tert-butyl ester

HRID 908221
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HRID 908221 반응식
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[Br:18][C:19]1[C:20](C(O)=O)=[CH:21][C:22]2[N:23]([CH:25]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:27]=2)[CH:24]=1.C([N:39]([CH2:42]C)CC)C.[C:44]([OH:48])([CH3:47])([CH3:46])[CH3:45]>C(OCC)(=O)C>[C:44]([O:48][C:42](=[O:8])[NH:39][C:20]1[C:19]([Br:18])=[CH:24][N:23]2[CH:25]=[C:26]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:27]=[C:22]2[CH:21]=1)([CH3:47])([CH3:46])[CH3:45]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 670418506-Bromo-2-phenylimidazo[1,2-a]pyridine-7-carboxylic acid

생성물 1

HCID 67041813(6-Bromo-2-phenyl-imidazo[1,2-a]pyridin-7-yl)-carbamic acid tert-butyl ester수율 25%

시약·촉매·용매 1

HCID 8857
Ethyl Acetate
용매

실험 절차

Under an atmosphere of argon, diphenylphosphoryl azide (8.20 g, 29 mmol) was added to a solution of 6-bromo-2-phenyl-imidazo[1,2-a]pyridine-7-carboxylic acid (9.16 g, 29 mmol) and triethylamine (5.8 g, 58 mmol) in tert-butanol (86 ml). The mixture was heated to reflux overnight, then cooled and diluted with ethyl acetate. The mixture was washed (NH4Cl satd.), and dried (Na2SO4). The title compound (2.75 g, 25%) was isolated from the residue by column chromatography (silica gel, heptane:ethyl acetate=100:0-50:50). MS (m/e)=388.1 [M+H+].

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. temperaturecooled
  4. washThe mixture was washed (NH4Cl satd.)
  5. dry with materialdried (Na2SO4)

출처 및 근거

ORD 기록
ord-63b26d619cc942f9b25f071a29566cf8
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08017604B2

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