Ethyl Acetate → 2-(2-tert-Butyl-phenoxy)-6-methoxy-pyridin-3-ylamine

HRID 555394Notes

Reaction equation

HRID 555394 reaction equation
[C:1]([C:5]1[CH:22]=[CH:21][CH:20]=[CH:19][C:6]=1[O:7][C:8]1[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[C:10]([O:17][CH3:18])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C.[H][H]>[Pd].CO>[C:1]([C:5]1[CH:22]=[CH:21][CH:20]=[CH:19][C:6]=1[O:7][C:8]1[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]([O:17][CH3:18])[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 598574032-(2-tert-Butyl-phenoxy)-6-methoxy-3-nitro-pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 598574072-(2-tert-Butyl-phenoxy)-6-methoxy-pyridin-3-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2a (580 mg, 1.9 mmol) in a 1:1 mixture of ethyl acetate and methanol (6 mL) was added palladium on charcoal (10% wt, 300 mg, 0.28 mmol). The mixture was stirred under 40 psi atmosphere of hydrogen. After 30 min, the solution was filtered over Celite® and the resulting solution was concentrated to afford the title compound 2b as a dark solution (500 mg, 96% yield). 2b was used in the next step without any further purification. [M+H]+=273.21. 1H NMR (500 MHz, CD3OD) δ ppm 1.43 (m, 9H), 3.58 (m, 3H), 6.33 (d, J=8.25 Hz, 1H), 6.93 (d, J=8.25 Hz, 1H), 7.09 (m, 2H), 7.17 (t, J=7.70 Hz, 1H), 7.41 (d, J=8.25 Hz, 1H).

Workup

  1. filtrationthe solution was filtered over Celite®
  2. concentrationthe resulting solution was concentrated

Sources & evidence

ORD record
ord-af3e52a7a33a45f78163c8e3dddec863
Source dataset
uspto-grants-2011_11
Patent number
US08053450B2

Reaction notes

Loading…