Ammonium Chloride → 6-[2-(Tert-butyl-dimethyl-silanyloxy)-ethylsulfanyl]-2-methyl-pyridin-3-ylamine

HRID 1811573Notes

Reaction equation

HRID 1811573 reaction equation
[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][CH2:7][CH2:8][S:9][C:10]1[N:15]=[C:14]([CH3:16])[C:13]([N+:17]([O-])=O)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-]>C1COCC1.[Zn]>[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][CH2:7][CH2:8][S:9][C:10]1[N:15]=[C:14]([CH3:16])[C:13]([NH2:17])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 25517Ammonium Chloride2×HCID 586715856-[2-(Tert-butyl-dimethyl-silanyloxy)-ethylsulfanyl]-2-methyl-3-nitro-pyridine

Product 1

HCID 586715776-[2-(Tert-butyl-dimethyl-silanyloxy)-ethylsulfanyl]-2-methyl-pyridin-3-ylamineYield 54%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-[2-(tert-butyl-dimethyl-silanyloxy)-ethylsulfanyl]-2-methyl-3-nitro-pyridine (80, 2.67 g, 8.1 mmol) in 15 mL THF, zinc dust (1.6 g, 24 mmol) followed by 8.2 mL (8.2 mmol) 1M NH4Cl solution was added. After stirring at room temperature for 3 h, more zinc dust (0.77 g, 8.13 mmol) and NH4Cl (0.43 g, 8.31 mmol) was added. After stirring for 4 h at mixture was filtered through celite and filtrate was extracted with CH2Cl2 and 1M NaOH. Organic phases were dried over MgSO4, filtered, and concentrated. Residue was purified by column chromatography (Hexane/AcOEt 3:1→2:1) to give 6-[2-(tert-butyl-dimethyl-silanyloxy)-ethylsulfanyl]-2-methyl-pyridin-3-ylamine as a yellowish oil (1.3 g, 54%). Exact mass calculated for C25H34BrN5O5 563.17. found 564.3 (MH+).

Workup

  1. additionwas added
  2. stirringAfter stirring for 4 h at mixture
  3. filtrationwas filtered through celite and filtrate
  4. extractionwas extracted with CH2Cl2 and 1M NaOH
  5. dry with materialOrganic phases were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customResidue was purified by column chromatography (Hexane/AcOEt 3:1→2:1)

Sources & evidence

ORD record
ord-48127dc283ff4b67b384e43a06c294ec
Source dataset
uspto-grants-2013_01
Patent number
US08362248B2

Reaction notes

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