Tert-butyl-[2-(2,3-difluoro-4-methyl-5-nitro-phenoxy)-ethoxy]-dimethyl-silane → 5-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-3,4-difluoro-2-methyl-phenylamine

HRID 2065747Notes

Reaction equation

HRID 2065747 reaction equation
[C:1]([Si:5]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[C:16]([N+:18]([O-])=O)[C:15]([CH3:21])=[C:14]([F:22])[C:13]=1[F:23])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([Si:5]([CH3:7])([CH3:6])[O:8][CH2:9][CH2:10][O:11][C:12]1[C:13]([F:23])=[C:14]([F:22])[C:15]([CH3:21])=[C:16]([NH2:18])[CH:17]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 59378019Tert-butyl-[2-(2,3-difluoro-4-methyl-5-nitro-phenoxy)-ethoxy]-dimethyl-silane

Product 1

HCID 593779115-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-3,4-difluoro-2-methyl-phenylamineYield 60.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of tert-butyl-[2-(2,3-difluoro-4-methyl-5-nitro-phenoxy)-ethoxy]-dimethyl-silane (1.16 g, 3.33 mmol) in EtOH (10 ml) was added 10% Pd/C (0.116 g) and the mixture was hydrogenated under balloon pressure for two hours. The mixture was filtered and the filtrate was concentrated to dryness under reduced pressure. Purification of the crude product by flash chromatography (hexanes:EtOAc 7:3) gave 0.638 g of 5-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-3,4-difluoro-2-methyl-phenylamine as a tan solid.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness under reduced pressure
  3. customPurification of the crude product by flash chromatography (hexanes:EtOAc 7:3)

Sources & evidence

ORD record
ord-c7936c35252b4ee380b4bc176719677b
Source dataset
uspto-grants-2012_10
Patent number
US08288552B2

Reaction notes

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