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

HRID 640135Notes

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

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

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

Sources & evidence

ORD record: ord-204552f11d9b48748ba862d63d855d89
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691882B2

Reaction notes

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