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Triphenylphosphine → 1-(2-Ethyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-(trifluoromethyl)-2-thienyl)methoxy)pyridin-2(1H)-one

HRID 2203103
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HRID 2203103 반응식
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH2:8][OH:9])[S:6][CH:7]=1.[CH2:12]([C:14]1[N:18]([CH3:19])[C:17]2[CH:20]=[C:21]([N:24]3[CH:29]=[CH:28][C:27](O)=[CH:26][C:25]3=[O:31])[CH:22]=[CH:23][C:16]=2[N:15]=1)[CH3:13].N(C(OCCOC)=O)=NC(OCCOC)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.O>[CH2:12]([C:14]1[N:18]([CH3:19])[C:17]2[CH:20]=[C:21]([N:24]3[CH:29]=[CH:28][C:27]([O:9][CH2:8][C:5]4[S:6][CH:7]=[C:3]([C:2]([F:10])([F:1])[F:11])[CH:4]=4)=[CH:26][C:25]3=[O:31])[CH:22]=[CH:23][C:16]=2[N:15]=1)[CH3:13]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 533844152-methoxyethyl N-(2-methoxyethoxycarbonylimino)carbamateHCID 896902462-Thiophenemethanol, 4-(trifluoromethyl)-HCID 896909981-(2-Ethyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one

생성물 1

HCID 896911371-(2-Ethyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-(trifluoromethyl)-2-thienyl)methoxy)pyridin-2(1H)-one
수율 8.6%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (4-(trifluoromethyl)thiophen-2-yl)methanol (50 mg) in THF (3 ml) were added 1-(2-ethyl-1-methyl-1H-benzo[d]imidazol-6-yl)-4-hydroxypyridin-2(1H)-one (73.9 mg), bis(2-methoxyethyl) azodicarboxylate (129 mg) and PPh3 (144 mg) at room temperature, and the mixture was stirred for 3 h. The mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed with saturated NaHCO3 solution and brine successively, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (EtOAc/MeOH) to give the title compound (10.2 mg) as white crystals.

후처리

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with saturated NaHCO3 solution and brine successively
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (EtOAc/MeOH)

출처 및 근거

ORD 기록
ord-90a9a1b6cb68402781c807ab66e7f61c
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365540B2

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