HCID 69620938, compound → HCID 67496653, compound

HRID 1628312Notes

Reaction equation

HRID 1628312 reaction equation
[CH3:1][C:2]([C:11]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[CH:14]=[C:13]([N+:23]([O-])=O)[CH:12]=1)([CH3:10])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]>[Pd].CO>[NH2:23][C:13]1[CH:12]=[C:11]([C:2]([CH3:10])([CH3:1])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[CH:14]=1

Participants

4

Reactant 1

HCID 69620938HCID 69620938, compound

Product 1

HCID 67496653HCID 67496653, compoundYield 66.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a 250 ml was added tert-butyl 2-methyl-2-(3-nitro-5-(pyridin-4-yl)phenyl)propanoate 63.1.A (1.9 g, 5.5 mmole) 4 g 10% of Pd/C and 50 ml of MeOH. The air from the reaction vessel was removed and purged with hydrogen gas via a balloon. This was repeated three times to ensure all air was removed from the reaction vessel. The reaction was stirred at room temperature under an atmosphere of hydrogen for 6 hours. The reaction mixture was filtered over a pad of celite (elute with MeOH) and the solvent removed to give tert-butyl 2-(3-amino-5-(pyridin-4-yl)phenyl)-2-methylpropanoate 63.1.B as a light brown solid (1.15 g, 66% yield).

Workup

  1. customThe air from the reaction vessel was removed
  2. custompurged with hydrogen gas via a balloon
  3. customwas removed from the reaction vessel
  4. filtrationThe reaction mixture was filtered over a pad of celite (elute with MeOH)
  5. customthe solvent removed

Sources & evidence

ORD record
ord-bb708ab7ad2e4dfa97e2a1676364afd9
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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