tert-Butyl(dimethyl)[(prop-2-yn-1-yl)oxy]silane → 3-((Tert-butyldimethylsilyloxy)methyl)-7-chloro-2,6-naphthyridine

HRID 1502412Notes

Reaction equation

Br[C:2]1[C:3]([CH:9]=[N:10][C:11]([CH3:14])([CH3:13])C)=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.[C:15]([Si:19]([CH3:25])([CH3:24])[O:20]CC#C)([CH3:18])([CH3:17])[CH3:16]>C(#N)C.C(Cl)Cl.[Zn]>[Si:19]([O:20][CH2:14][C:11]1[N:10]=[CH:9][C:3]2[C:2]([CH:13]=1)=[CH:7][N:6]=[C:5]([Cl:8])[CH:4]=2)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of N-((5-bromo-2-chloropyridin-4-yl)methylene)-2-methylpropan-2-amine (530 mg, 1.9 mmol), tert-butyldimethyl(2-propynyloxy)silane (0.59 mL, 2.9 mmol), NiCl2(DPPP) (52 mg, 0.1 mmol), and zinc (252 mg, 3.9 mmol) in acetonitrile (5 mL) was heated at 70° C. under an atmosphere of nitrogen. The cooled reaction mixture was diluted with methylene chloride (50 mL), filtered over Celite, and evaporated in vacuo to afford a residue that was purified by flash chromatography (silica, 12 g, ISCO, 0-40% ethyl acetate in heptane) to afford the title compound as an orange waxy solid (340 mg, 57%), which was used in the next step without further purification.

Workup

customThe cooled reaction mixture
filtrationfiltered over Celite
customevaporated in vacuo
customto afford a residue that
customwas purified by flash chromatography (silica, 12 g, ISCO, 0-40% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-7672f6d270644f3d9bfc2eaae01c3cbf
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206175B2

Reaction notes

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