tert-Butyl {3-[(2-morpholin-4-yl-5-nitrophenyl)ethynyl]phenyl}carbamate → tert-Butyl {3-[2-(5-amino-2-morpholin-4-ylphenyl)ethyl]phenyl}carbamate

HRID 541955Notes

Reaction equation

HRID 541955 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=2[C:16]#[C:17][C:18]2[CH:19]=[C:20]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:21]=[CH:22][CH:23]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>CO.[Pd]>[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)=[C:8]([CH2:16][CH2:17][C:18]2[CH:19]=[C:20]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:21]=[CH:22][CH:23]=2)[CH:9]=1

Participants

4

Reactant 1

HCID 57962728tert-Butyl {3-[(2-morpholin-4-yl-5-nitrophenyl)ethynyl]phenyl}carbamate

Product 1

HCID 57961954tert-Butyl {3-[2-(5-amino-2-morpholin-4-ylphenyl)ethyl]phenyl}carbamateYield 93.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl {3-[(2-morpholin-4-yl-5-nitrophenyl)ethynyl]phenyl}carbamate (0.33 g, 0.78 mmol) in methanol (20 mL) was degassed with nitrogen, treated with 10% palladium on carbon (wet Degussa type) (0.33 g, 100 wt %), degassed with nitrogen, and shaken under an atmosphere of hydrogen (50 psi) for 48 h. The reaction mixture was filtered over celite and the filtrate concentrated to give the desired product (0.29 g, 92%) which was used without further purification. LCMS for C23H32N3O3 (M+H)+: m/z=398.1.

Workup

  1. customdegassed with nitrogen
  2. filtrationThe reaction mixture was filtered over celite
  3. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-ddfc5ad4b4bc476c8bf739e0945c93b6
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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