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

HRID 475121ノート

反応式

HRID 475121 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
85 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-3ca3fa32512e4f80bcbf3ea31b984ebb
出典データセット
uspto-grants-2014_01
特許番号
US08637537B2

反応ノート

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