3,4-dihydro-2H-pyran → methyl 1-(tetrahydro-2H-pyran-2-yl)-1H-benzimidazole-5-carboxylate

HRID 475172노트

반응식

HRID 475172 반응식
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:9][C:4]=2[N:3]=[CH:2]1.[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1>CC1C=CC(S(O)(=O)=O)=CC=1.O.C1COCC1>[O:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:9][C:4]=2[N:3]=[CH:2]1

참가 물질

5

반응물 2

HCID 80803,4-dihydro-2H-pyranHCID 178497374HCID 178497374, 화합물

생성물 1

HCID 58324962methyl 1-(tetrahydro-2H-pyran-2-yl)-1H-benzimidazole-5-carboxylate수율 96%

시약·촉매·용매 2

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 8028Tetrahydrofuran용매

실험 절차

A round-bottom flask was charged with 20 (1.76 g, 10 mmol), p-TsOH.H2O (38 mg, 0.2 mmol), 3,4-dihydro-2H-pyran (1.26 g, 15 mmol) and THF (20 mL). The reaction mixture was degassed with nitrogen and heated at reflux for 18 h, and then the solvent was removed under reduced pressure. The residue was diluted with DCM (250 mL) and water (50 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with a DCM/MeOH gradient (0.5 to 1.0% MeOH) to afford 2.5 g (90%) of methyl 1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-5-carboxylate (22) as a grey oil: MS (ESI) m/z=261.2 [M+1]+.

후처리

  1. customThe reaction mixture was degassed with nitrogen
  2. temperatureheated
  3. temperatureat reflux for 18 h
  4. customthe solvent was removed under reduced pressure
  5. additionThe residue was diluted with DCM (250 mL) and water (50 mL)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by SiO2 chromatography
  10. washeluting with a DCM/MeOH gradient (0.5 to 1.0% MeOH)

출처 및 근거

ORD 기록
ord-bc753d52187c427eb2bf0da212da4ee9
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637537B2

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