3-({[tert-Butyl(diphenyl)silyl]oxy}methyl)-1-(2-chloro-4-nitrophenyl)pyridin-2(1H)-one → 1-(4-Amino-2-chlorophenyl)-3-({[tert-butyl(diphenyl)silyl]oxy}methyl)pyridin-2(1H)-one

HRID 85196Notes

Reaction equation

HRID 85196 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[C:21](=[O:36])[N:22]([C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[CH:28][C:27]=2[Cl:35])[CH:23]=[CH:24][CH:25]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C1COCC1.[Pd]>[NH2:32][C:29]1[CH:30]=[CH:31][C:26]([N:22]2[CH:23]=[CH:24][CH:25]=[C:20]([CH2:19][O:18][Si:1]([C:14]([CH3:15])([CH3:17])[CH3:16])([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:21]2=[O:36])=[C:27]([Cl:35])[CH:28]=1

Participants

5

Reactant 2

HCID 594101863-({[tert-Butyl(diphenyl)silyl]oxy}methyl)-1-(2-chloro-4-nitrophenyl)pyridin-2(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 594101581-(4-Amino-2-chlorophenyl)-3-({[tert-butyl(diphenyl)silyl]oxy}methyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

800 mg (1.54 mmol) of the compound from Example 4A are dissolved in 48 ml of THF. 50 mg (0.05 mmol) of palladium on carbon are then added, and the mixture is hydrogenated at RT in a hydrogen atmosphere under atmospheric pressure. The mixture is then filtered, the filter cake is washed with THF and the filtrate is freed from the solvent. The reaction product (purity: 95%) is reacted further without further purification.

Workup

  1. filtrationThe mixture is then filtered
  2. washthe filter cake is washed with THF
  3. customThe reaction product (purity: 95%) is reacted further without further purification

Sources & evidence

ORD record
ord-0dc9decdcb29431d89d872f68fffee9c
Source dataset
uspto-grants-2014_09
Patent number
US08846934B2

Reaction notes

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