Water → 3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile

HRID 475121노트

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HRID 475121 반응식
[I:1][C:2]1[C:10]2[C:9]([C:11]#[N:12])=[CH:8][CH:7]=[CH:6][C:5]=2[NH:4][N:3]=1.[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1.CC1C=CC(S(O)(=O)=O)=CC=1.O>C1COCC1>[I:1][C:2]1[C:10]2[C:9]([C:11]#[N:12])=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][O:13]2)[N:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 1785096383-Iodo-1H-indazole-4-carbonitrile

생성물 1

HCID 712725503-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile수율 84.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
85 °C

실험 절차

A mixture of 3-iodo-1H-indazole-4-carbonitrile (3.0 g, 11.1 mmol), dihydropyran (1.84 g, 22.2 mmol), and TsOH (212 mg, 1.1 mmol) under nitrogen in THF (40 mL) was heated at 85° C. overnight. Water (40 mL) was added and the mixture was extracted with EtOAc (50 mL×3). The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (5:1) to afford 3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile as white solid (3.31 g, 84.0%). MS (ESI): m/z=354 [M+1]+.

후처리

  1. extractionthe mixture was extracted with EtOAc (50 mL×3)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by SiO2 chromatography
  7. washeluting with petroleum ether/EtOAc (5:1)

출처 및 근거

ORD 기록
ord-3ca3fa32512e4f80bcbf3ea31b984ebb
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637537B2

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