Azidotrimethylsilane → HCID 178489101, compound

HRID 33931

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.C[Si]([N:21]=[N+:22]=[N-:23])(C)C>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[NH:23][N:22]=[N:21][C:10]=2[C:11]2[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=2)=[CH:7][CH:8]=1

Participants

Reactant 2

HCID 78378Azidotrimethylsilane

HCID 45952534-[2-(4-Methoxyphenyl)ethynyl]pyridine

Product 1

HCID 178489101HCID 178489101, compoundYield 53%

Conditions

Temperature: 150 °C

Procedure

4-(2-(4-methoxyphenyl)ethynyl)pyridine (1.48 g, 7.1 mmol) and trimethylsilylazide (2.5 g, 21.3 mmol) were combined in a sealed tube which was heated 48 h in a 150° C. oil bath. The mixture was chromatographed on silica using an ethyl acetate-hexanes gradient giving a yellow solid (950 mg, 53%). 1H NMR (CDCl3, 400 mHz) δ 8.50 (d, 2H, J=5.8 Hz), 7.60 (d, 2H, J=5.8 Hz), 7.36 (d, 2H, J=8.7 Hz), 6.92 (d, 2H, J=8.7 Hz), 3.81 (s, 3H), 2.80 (br, 1H). MS (AP+) m/e 253 (MH+).

Workup

customThe mixture was chromatographed on silica using an ethyl acetate-hexanes gradient

Sources & evidence

ORD record: ord-fbfc539e405f4b0a87a9c6ec5d541498
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429665B2

Linked notes

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