Water → 5-(2-(Trimethylsilyl)ethynyl)pyridin-2-amine

HRID 1693808Notes

Reaction equation

HRID 1693808 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][Si:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][N:5]=1)([O-])=O.O.[Cl-].[NH4+]>O1CCCC1.[Fe]>[CH3:13][Si:12]([C:11]#[C:10][C:7]1[CH:8]=[CH:9][C:4]([NH2:1])=[N:5][CH:6]=1)([CH3:14])[CH3:15]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 580762652-Nitro-5-((trimethylsilyl)ethynyl)pyridine

Product 1

HCID 224828585-(2-(Trimethylsilyl)ethynyl)pyridin-2-amineYield 91.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-nitro-5-trimethylsilanylethynyl-pyridine (405 mg, 1.84 mmol) described in Manufacturing Example 28-1-1 in tetrahydrofuran (10 mL) and water (5 mL) were added iron powder (514 mg, 9.21 mmol) and ammonium chloride (197 mg, 3.69 mmol) at room temperature, which was stirred for 75 minutes at 70° C. The reaction solution was cooled to room temperature and filtered through a Celite pad, and the filtrate was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the title compound (319 mg, 91%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. filtrationfiltered through a Celite pad
  3. concentrationthe filtrate was concentrated under a reduced pressure
  4. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-13da2bd97e5c4b15891b7a62c1df511b
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

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