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

HRID 1927214Notes

Reaction equation

C1COCC1.[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][Si:17]([CH3:20])([CH3:19])[CH3:18])=[CH:11][N:10]=1)([O-])=O.[Cl-].[NH4+]>[Fe].O>[CH3:18][Si:17]([C:16]#[C:15][C:12]1[CH:13]=[CH:14][C:9]([NH2:6])=[N:10][CH:11]=1)([CH3:19])[CH3:20]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of THF (10 mL) and water (5 mL) of 2-nitro-5-trimethylsilanylethynyl-pyridine (410 mg) described in Manufacturing Example 3-1 were added iron powder (510 mg) and ammonium chloride (200 mg) at room temperature, which was stirred for 75 minutes at 70° C. The reaction solution was cooled to room temperature, and then filtered through Celite, and the solvent was evaporated from the filtrate under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the titled compound (320 mg).

Workup

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

Sources & evidence

ORD record: ord-9e85d9cc82eb4454af3bd18345f83325
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183264B2

Reaction notes

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