Tributylphosphine → 1-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-((3-fluorobenzyl)oxy)pyridin-2(1H)-one

HRID 2202953노트

반응식

HRID 2202953 반응식
[CH:1]1([C:4]2[N:5]=[C:6]3[CH:11]=[CH:10][C:9]([N:12]4[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]4=[O:19])=[CH:8][N:7]3[C:20]=2[CH3:21])[CH2:3][CH2:2]1.[F:22][C:23]1[CH:24]=[C:25]([CH2:29]O)[CH:26]=[CH:27][CH:28]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1>[CH:1]1([C:4]2[N:5]=[C:6]3[CH:11]=[CH:10][C:9]([N:12]4[CH:17]=[CH:16][C:15]([O:18][CH2:29][C:25]5[CH:26]=[CH:27][CH:28]=[C:23]([F:22])[CH:24]=5)=[CH:14][C:13]4=[O:19])=[CH:8][N:7]3[C:20]=2[CH3:21])[CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 13831TributylphosphineHCID 680083-Fluorobenzylic alcoholHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 896902811-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one

생성물 1

HCID 897024001-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-((3-fluorobenzyl)oxy)pyridin-2(1H)-one수율 21.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

To a solution of 1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one (150 mg), (3-fluorophenyl)-methanol (134 mg) and tributylphosphine (322 mg) in THF (15 ml) was added 1,1′-(azodicarbonyl)dipiperidine (401 mg). The mixture was stirred under sonication at 60° C. for 4 h. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The residue was diluted with DCM (100 ml), and the DCM layer was washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM) to give the title compound (45 mg) as a white solid.

후처리

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with DCM (100 ml)
  4. washthe DCM layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (MeOH/DCM)

출처 및 근거

ORD 기록
ord-384689d7c9e7490b994636fbf0e5a378
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365540B2

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