3,4-dihydro-2H-pyran → 6-chloro-2-(tetrahydro-2H-pyran-2-yl)-2H-pyrazolo[4,3-c]pyridine

HRID 57883Notes

Reaction equation

HRID 57883 reaction equation
ClC1N=CC2C=NNC=2C=1.O1C=CCCC1.[Cl:17][C:18]1[N:23]=[CH:22][C:21]2[CH:24]=[N:25][N:26]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)[C:20]=2[CH:19]=1>O1CCOCC1.S(O)(C1C=CC(C)=CC=1)(=O)=O>[Cl:17][C:18]1[N:23]=[CH:22][C:21]2=[CH:20][N:26]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)[N:25]=[C:24]2[CH:19]=1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 569321096-Chloro-1H-pyrazolo(4,3-c)pyridineHCID 714636356-Chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 899145646-chloro-2-(tetrahydro-2H-pyran-2-yl)-2H-pyrazolo[4,3-c]pyridineYield 76%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 6-chloro-1H-pyrazolo[4,3-c]pyridine (11.5 g, 0.075 mol) and 3,4-dihydro-2H-pyran (19 g, 0.225 mol) and Tos-OH (0.13 g 0.75 mmol) in 1,4-dioxane (175 mL) was heated at 110° C. overnight. The mixture was cooled to room temperature and concentrated. The crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 20:0˜20:1) to afford a mixture of 6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine and 6-chloro-2-(tetrahydro-2H-pyran-2-yl)-2H-pyrazolo[4,3-c]pyridine (13.5 g, yield 76%) MS (ESI) m/z: m/z: 238 [M+H]+

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customThe crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 20:0˜20:1)
  4. customto afford

Sources & evidence

ORD record
ord-4b4f12f419bd43c78b541e598103a6f5
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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