Methanol → {4-[2-(2-Methoxy-phenyl)-ethyl]-pyridin-2-yl}-carbamic acid tert-butyl ester

HRID 1023447Notes

Reaction equation

HRID 1023447 reaction equation
CO.[C:3]([O:7][C:8](=[O:26])[NH:9][C:10]1[CH:15]=[C:14]([C:16]#[C:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])[CH:13]=[CH:12][N:11]=1)([CH3:6])([CH3:5])[CH3:4]>C(OCC)(=O)C.[Pd]>[C:3]([O:7][C:8](=[O:26])[NH:9][C:10]1[CH:15]=[C:14]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])[CH:13]=[CH:12][N:11]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 2

HCID 887MethanolHCID 69085398[4-(2-Methoxy-phenylethynyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

Product 1

HCID 69085786{4-[2-(2-Methoxy-phenyl)-ethyl]-pyridin-2-yl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methanol (10 mL) and Pd/C (100 mg) are added to a solution of [4-(2-methoxy-phenylethynyl)-pyridin-2-yl]-carbamic acid tert-butyl ester (146 mg, 0.450 mmol) in ethyl acetate (10 mL). The mixture is evacuated and purged with H2 (three times), and stirred at the room temperature under an atmosphere of H2 for 2 hours. The mixture is evacuated and purged with Argon, and filtered through a pad of diatomaceous earth. The filtrate is concentrated to give the crude product, which is used in the next step without purification.

Workup

  1. customThe mixture is evacuated
  2. custompurged with H2 (three times)
  3. customThe mixture is evacuated
  4. custompurged with Argon
  5. filtrationfiltered through a pad of diatomaceous earth
  6. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-8c3a5cb765bf4453ba0ee85f577c28ca
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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