Ethanol → 3-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile

HRID 475141

Reaction equation

HRID 475141 reaction equation
I[C:2]1[C:10]2[C:9]([C:11]#[N:12])=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[N:3]=1.CC1C=NC2C(C=1C)=CC=C1C=2N=CC(C)=C1C.C[CH2:38][OH:39]>[Cu]I>[CH3:38][O:39][C:2]1[C:10]2[C:9]([C:11]#[N:12])=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[N:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineHCID 71272550HCID 71272550, compound

Product 1

HCID 712722393-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrileYield 35.7%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
90 °C

Procedure

A mixture of 3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile (50 mg, 0.142 mmol), CuI (13.5 g 0.071 mmol), CsCO3 (2.7 mg, 0.0142 mmol), and 3,4,7,8-tetramethyl-1,10-phenanthroline (0.0142 mg, 3.5 mmol) in EtOH (0.5 mL) under nitrogen in a sealed vial was heated to 90° C. in a microwave oven for 100 min. The reaction mixture was quenched with water and extracted with EtOAc. The extract was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with petroleum ether:EtOAc to afford 3-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile as white solid (13 mg, 35.7%). MS (ESI): m/z=258 [M+1]+.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc
  3. dry with materialThe extract was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by SiO2 chromatography
  7. washeluting with petroleum ether

Sources & evidence

ORD record
ord-e03f189af0724914bfbf36403b22ab3f
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Linked notes

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