4-Fluorophenol → 1-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-((4-fluorophenoxy)methyl)pyridin-2(1H)-one

HRID 2202991노트

반응식

HRID 2202991 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]([CH2:18][OH:19])=[CH:14][C:13]4=[O:20])=[CH:8][N:7]3[C:21]=2[CH3:22])[CH2:3][CH2:2]1.[F:23][C:24]1[CH:29]=[CH:28][C:27](O)=[CH:26][CH:25]=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]([CH2:18][O:19][C:27]5[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=5)=[CH:14][C:13]4=[O:20])=[CH:8][N:7]3[C:21]=2[CH3:22])[CH2:2][CH2:3]1

참가 물질

6

반응물 4

HCID 97324-FluorophenolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 89690337HCID 89690337, 화합물

생성물 1

HCID 896901851-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-((4-fluorophenoxy)methyl)pyridin-2(1H)-one수율 12.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

To a solution of 1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-(hydroxymethyl)pyridin-2(1H)-one (150 mg), 4-fluorophenol (85 mg) and tributylphosphine (307 mg) in THF (20 ml) was added 1,1′-(azodicarbonyl)dipiperidine (386 mg), and the mixture was stirred at 60° C. for 5 h. The reaction mixture was cooled to room temperature, concentrated in vacuo, and diluted with DCM. The mixture was washed with water and brine successively, dried over Na2SO4, concentrated in vacuo and purified by column chromatography (MeOH/DCM) followed by preparative HPLC to afford the title compound (24 mg) as a white solid.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additiondiluted with DCM
  4. washThe mixture was washed with water and brine successively
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography (MeOH/DCM)

출처 및 근거

ORD 기록
ord-5c701066adfc4d5c99c1c178d08b2582
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365540B2

반응 노트

불러오는 중…