HCID 66712636, compound → 955369-50-3

HRID 1778997Notes

Reaction equation

HRID 1778997 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[C:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=1>CN(C=O)C.[Pd]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:13][CH2:12]2)=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 1

HCID 66712636HCID 66712636, compound

Product 1

HCID 58166533955369-50-3

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of tert-butyl 4-(2-methyl-4-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate (A38) (211 mg, 0.663 mmol) in DMF (7.5 mL) was added a slurry of 10% Pd/C (100 mg) in DMF (0.5 mL) and the resulting mixture was stirred for 16 hours under a hydrogen atmosphere at room temperature. The resulting mixture was filtered through Celite then the volatiles were removed under reduced pressure. The residue was purified by silica gel column chromatography (Biotage Isolera, SiO2 cartridge, 0-60% EtOAc in petroleum benzine 40-60° C.) to give the title compound A39 as a pale orange solid (185 mg, 96%); 1H NMR (400 MHz, CDCl3) δ 6.95 (d, J=8.0 Hz, 1H), 6.56-6.48 (m, 2H), 3.51 (s, 2H), 2.88-2.65 (m, 3H), 2.26 (s, 3H), 1.74-1.66 (m, 2H), 1.63-1.51 (m, obscured by solvent), 1.48 (s, 9H).

Workup

  1. filtrationThe resulting mixture was filtered through Celite
  2. customthe volatiles were removed under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (Biotage Isolera, SiO2 cartridge, 0-60% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-0d4c18c180f24b9893d9b76a9e6193d7
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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