HCID 59853070, compound → HCID 59852997, compound

HRID 2373992Notes

Reaction equation

HRID 2373992 reaction equation
[F:1][C:2]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[CH:11]=[CH2:12]>[C].[Pd].CCOC(C)=O.CO>[CH2:11]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:5]=1[O:4][C:3]1[CH:13]=[CH:14][C:15]([NH2:17])=[CH:16][C:2]=1[F:1])[CH3:12]

Participants

4

Reactant 1

HCID 59853070HCID 59853070, compound

Product 1

HCID 59852997HCID 59852997, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution of 4-(2-fluoro-4-nitrophenoxy)-3-vinylpyridine (80 mg, 0.30 mmol) in 1:1 EtOAc/MeOH (2 mL) was hydrogenated over 10% palladium-carbon (30 mg) for 1 h using H2 from a latex balloon. Pt2O (10 mg) was added to the mixture and the reaction continued for 1 h. The mixture was filtered through Celite® and concentrated in vacuo to give the title compound (50 mg, 63%) as a yellow oil. 1H NMR (DMSO-d6) δ 8.33 (s, 1H), 8.22 (d, 1H, J=5.6 Hz), 6.96 (dd, 1H, J=8.7, 9.1 Hz), 6.50 (dd, 1H, J=2.0, 13.7 Hz), 6.56 (d, 1H, J=5.6 Hz), 6.41 (dd, 1H, J=2.5, 6.1 Hz), 2.69 (q, 2H, J=7.6 Hz), 1.21 (t, 31H, J=7.6 Hz).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-203e541767ab4114b38184a22caab9ea
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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