HCID 66625257, compound → HCID 58286296, compound

HRID 417350Notes

Reaction equation

HRID 417350 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]([N+:20]([O-])=O)=[CH:14][N:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:4]([Si:1]([CH3:3])([CH3:2])[O:8][CH2:9][CH2:10][O:11][C:12]1[N:13]=[CH:14][C:15]([NH2:20])=[C:16]([O:18][CH3:19])[CH:17]=1)([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 1

HCID 66625257HCID 66625257, compound

Product 1

HCID 58286296HCID 58286296, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Step BA suspension of 2-(2-(tert-butyldimethylsilyloxy)ethoxy)-4-methoxy-5-nitropyridine (0.9 g, 2.7 mmol) and Pd/C (Aldrich, 10%, 0.15 g) in ethyl acetate (10 mL) was vigorously shaken in a Parr under atmosphere of H2 (50 psi) for 45 min. The mixture was filtered through a short pad of celite. The filtrate was concentrated to give 6-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-4-methoxy-pyridin-3-ylamine as a off white gum (0.6 g, 73%).

Workup

  1. filtrationThe mixture was filtered through a short pad of celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4bde44db0adf4ccbafbd5d9fa66662e9
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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