HCID 69037395, compound → HCID 69037490, compound

HRID 1865169Notes

Reaction equation

HRID 1865169 reaction equation
[C:1]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([N+:18]([O-])=O)=[CH:15][CH:16]=2)[CH:11]=[C:10]1[C:21]([O:23][CH2:24][CH3:25])=[O:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.[Pd]>[NH2:18][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[N:9]([C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:10]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:11]2

Participants

4

Reactant 1

HCID 69037395HCID 69037395, compound

Product 1

HCID 69037490HCID 69037490, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.2 (1.86 g, 5.5 mmol) and 10% Pd/C (440 mg) in dry THF (30 ml) was stirred under H2 for 16 hrs. The resulting mixture was filtered through celite which was washed with EtOAc (40 ml) and the filtrate was concentrated. The residue was purified by chromatography (SiO2, 0 to 40% EtOAc in hexanes) to afford 3.3 (1.63 g, 96%) as a bright yellow oil. 1H NMR (250 MHz, CDCl3) δ ppm 7.40-7.72 (m, 6H), 7.18 (s, 1H), 6.92 (d, 1H), 6.82 (dd, 1H), 3.92 (q, 2H), 3.68 (br s, 2H), 1.06 (t, 3H); FABMS: (NBA/NaI) m/z 308 (M+H+ expected 308).

Workup

  1. filtrationThe resulting mixture was filtered through celite which
  2. washwas washed with EtOAc (40 ml)
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by chromatography (SiO2, 0 to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7e1e5db0926c48829f1c6b38d965b2cc
Source dataset
uspto-grants-2009_12
Patent number
US07626026B2

Reaction notes

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