HCID 57962721, compound → HCID 57961604, compound

HRID 541859Notes

Reaction equation

HRID 541859 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[N:15]=[C:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1>CO.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[N:15]=[C:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 57962721HCID 57962721, compound

Product 1

HCID 57961604HCID 57961604, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of tert-butyl {6-[(3-aminophenyl)ethynyl]pyridin-2-yl}carbamate (70.0 mg, 2.3 mmol) in methanol (25 mL) and was added 10% palladium on carbon (700 mg, 0.60 mmol). The resultant mixture was hydrogenated at 60 psi for 3 hours. The reaction mixture was filtered, washed with MeOH and concentrated to give the desired product (680 mg, 96%). LCMS for C18H24N3O2 (M+H)+: m/z=314.1.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with MeOH
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-496f870fe3cc469fb19a3cb7cc0c8c35
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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