HCID 71114832, compound → HCID 71136990, compound

HRID 1624050Notes

Reaction equation

HRID 1624050 reaction equation
[NH:1]1[C:9]2[CH2:8][CH2:7][CH:6]=[C:5]([C:10]3[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([F:18])[CH:11]=3)[C:4]=2[CH:3]=[N:2]1.[H][H]>CO>[F:18][C:12]1[CH:11]=[C:10]([CH:5]2[CH2:6][CH2:7][CH2:8][C:9]3[NH:1][N:2]=[CH:3][C:4]2=3)[CH:17]=[CH:16][C:13]=1[C:14]#[N:15]

Participants

4

Reactant 2

HCID 71114832HCID 71114832, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 71136990HCID 71136990, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(6,7-Dihydro-1H-indazol-4-yl)-2-fluoro-benzonitrile (0.102 g, 0.43 mmol) 5% Pd/C wt/wt % (0.04 g) is added to MeOH (5.0 mL) and the mixture is stirred under 45-35 psi of hydrogen for 3 hours. The mixture is filtered through a plug of diatomaceous earth and concentrated to dryness. The residue is purified by silica gel chromatography eluting with 1:1 hexanes/ethyl acetate to give the title compound (0.021 g, 18%). ES/MS m/z 242 (M+H).

Workup

  1. filtrationThe mixture is filtered through a plug of diatomaceous earth
  2. concentrationconcentrated to dryness
  3. customThe residue is purified by silica gel chromatography
  4. washeluting with 1:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-0d88eca908a448fcabb23b7033fb7f63
Source dataset
uspto-grants-2014_07
Patent number
US08778984B2

Reaction notes

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