Tetrahydrofuran → HCID 178509558, compound

HRID 1624048Notes

Reaction equation

HRID 1624048 reaction equation
[N:1]1[NH:2][CH:3]=[C:4]2[C:9]=1[CH2:8][CH2:7][CH:6]=[C:5]2[C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1.C1COCC1>[Pd].CO>[N:1]1[NH:2][CH:3]=[C:4]2[C:9]=1[CH2:8][CH2:7][CH2:6][CH:5]2[C:10]1[CH:11]=[CH:12][C:13]([C:14]#[N:15])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 178509557HCID 178509557, compound

Product 1

HCID 178509558HCID 178509558, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-(6,7-dihydro-2H-indazol-4-yl)benzonitrile (3.21 g, 14.5 mmol) is added to THF (10 mL), MeOH (10 mL), and 5% Pd/C (0.2 g) and hydrogenated under a balloon of H2 at room temperature for two hours. The mixture is filtered through a pad of diatomaceous earth and evaporated to dryness. The residue is purified by silica gel flash chromatography eluting with 50%-70% ethyl acetate/hexanes, to give the title compound (3.15 g, 97%).

Workup

  1. filtrationThe mixture is filtered through a pad of diatomaceous earth
  2. customevaporated to dryness
  3. customThe residue is purified by silica gel flash chromatography
  4. washeluting with 50%-70% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-56f61da626e244a3b4754c47af582f5e
Source dataset
uspto-grants-2014_07
Patent number
US08778984B2

Reaction notes

Loading…