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Tributylphosphine → HCID 89691170, 화합물

HRID 2203075
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인쇄 미리보기

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HRID 2203075 반응식
[CH:1]1([C:4]2[N:8]([CH3:9])[C:7]3[CH:10]=[C:11]([N:14]4[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]4=[O:21])[CH:12]=[CH:13][C:6]=3[N:5]=2)[CH2:3][CH2:2]1.[Br:22][C:23]1[S:27][CH:26]=[C:25]([CH2:28]O)[CH:24]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1>[Br:22][C:23]1[S:27][CH:26]=[C:25]([CH2:28][O:20][C:17]2[CH:18]=[CH:19][N:14]([C:11]3[CH:12]=[CH:13][C:6]4[N:5]=[C:4]([CH:1]5[CH2:2][CH2:3]5)[N:8]([CH3:9])[C:7]=4[CH:10]=3)[C:15](=[O:21])[CH:16]=2)[CH:24]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 19006171(5-Bromothiophen-3-yl)methanolHCID 896910841-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one

생성물 1

HCID 89691170HCID 89691170, 화합물수율 30.7%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
60 °C

실험 절차

To a solution of 1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one (98 mg), (5-bromo-3-thienyl)methanol (135 mg) and tributylphosphine (211 mg) in THF (3 ml) was added 1,1′-(azodicarbonyl)dipiperidine (264 mg), and the reaction mixture was stirred at 60° C. for 3 h. The reaction mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc then EtOAc/MeOH). The resulting solid was recrystallized from EtOH-water to give the title compound (48.8 mg) as a white solid.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by silica gel column chromatography (hexane/EtOAc
  3. customThe resulting solid was recrystallized from EtOH-water

출처 및 근거

ORD 기록
ord-947e0da0fde444c09c7dc4184d2a207c
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365540B2

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