HCID 57961596, compound → tert-Butyl {2-[2-(3-aminophenyl)ethyl]pyridin-4-yl}carbamate

HRID 541842Notes

Reaction equation

HRID 541842 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:15]=[C:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:12][N: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[CH:15]=[C:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 57961596HCID 57961596, compound

Product 1

HCID 57962008tert-Butyl {2-[2-(3-aminophenyl)ethyl]pyridin-4-yl}carbamateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of tert-butyl {2-[(3-aminophenyl)ethynyl]pyridin-4-yl}carbamate (250 mg, 1.62 mmol) (prepared in Example C12, step A) in methanol (10 mL) was added 10% palladium on carbon (0.30 g, 0.24 mmol). The reaction mixture was hydrogenated at 50 psi overnight. The resultant mixture was filtered and concentrated to provide the desired product (240 mg, 95%) as a white solid. LCMS for C18H24N3O2 (M+H)+: m/z=314.0.

Workup

  1. customwas hydrogenated at 50 psi overnight
  2. filtrationThe resultant mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9260dea853494d6cb6f944618256c05a
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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