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

HRID 77853Notes

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-ef31e16dff0d4519ac429f7d017bd838
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841327B2

Reaction notes

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