Ammonium formate → 4-{2(R)-[2-(tert-Butyl-dimethyl-silanyloxy)-2-pyridin-3-yl-ethylamino]-2-methyl-propyl}-phenylamine

HRID 495717Notes

Reaction equation

HRID 495717 reaction equation
[C:1]([Si:5]([CH3:31])([CH3:30])[O:6][C@H:7]([C:23]1[CH:24]=[N:25][C:26](Cl)=[CH:27][CH:28]=1)[CH2:8][NH:9][C:10]([CH3:22])([CH3:21])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO.[Pd]>[C:1]([Si:5]([CH3:31])([CH3:30])[O:6][C@H:7]([C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)[CH2:8][NH:9][C:10]([CH3:21])([CH3:22])[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 20826856[2(R)-(tert-butyl-dimethyl-silanyloxy)-2-(6-chloro-pyridin-3-yl)-ethyl]-[1,1-dimethyl-2-(4-nitro-phenyl)-ethyl]-amine

Product 1

HCID 697452774-{2(R)-[2-(tert-Butyl-dimethyl-silanyloxy)-2-pyridin-3-yl-ethylamino]-2-methyl-propyl}-phenylamineYield 94.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a slurry of [2(R)-(tert-butyl-dimethyl-silanyloxy)-2-(6-chloro-pyridin-3-yl)-ethyl]-[1,1-dimethyl-2-(4-nitro-phenyl)-ethyl]-amine (8.0 g) and 10% palladium-on-carbon (4.0 g) in MeOH (200 mL) was added ammonium formate (22 g) and the resulting mixture was stirred at ambient temperature for 3 h. The reaction mixture was filtered through Celite®, washing with MeOH and the filtrate concentrated in vacuo. The resulting semi-solid was partitioned between ethyl acetate and half-saturated aqueous sodium bicarbonate, the organic phase was separated, dried (Na2SO4) and concentrated in vacuo to afford 6.5 g of the title compound (I-2g) as a dark oil.

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. washwashing with MeOH
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe resulting semi-solid was partitioned between ethyl acetate and half-saturated aqueous sodium bicarbonate
  5. customthe organic phase was separated
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-80805e502cfb4524a94f0c426755890c
Source dataset
uspto-grants-2005_09
Patent number
US06939867B2

Reaction notes

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