Tert-butyl {4-[(3-aminophenyl)ethynyl]pyridin-2-yl}carbamate → Tert-butyl {4-[2-(3-aminophenyl)ethyl]pyridin-2-yl}carbamate

HRID 541851Notes

Reaction equation

HRID 541851 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:11]=2)[CH:5]=[CH:6][CH:7]=1>CO.C(Cl)Cl.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 57961655Tert-butyl {4-[(3-aminophenyl)ethynyl]pyridin-2-yl}carbamate

Product 1

HCID 57961683Tert-butyl {4-[2-(3-aminophenyl)ethyl]pyridin-2-yl}carbamateYield 98.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl {4-[(3-aminophenyl)ethynyl]pyridin-2-yl}carbamate (328 mg, 1.06 mmol) in methanol (8 mL) and methylene chloride (8 mL) was added 10% palladium on carbon (100 mg, 0.09 mmol). The resultant mixture was hydrogenated at 30 psi for 18 hours. The reaction mixture was filtered, washed with MeOH/DCM and concentrated to give the desired product (326 mg, 98%) as a light brown powder. LCMS for C18H24N3O2 (M+H)+: m/z=314.1.

Workup

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

Sources & evidence

ORD record
ord-80f2e9dfece3464fa50851d52066f5b7
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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