tert-butyl N-methyl-N-(prop-2-yn-1-yl)carbamate → tert-butylmethyl(3-(5-(4-(tetrahydro-2H-pyran-2-yloxy)benzoyl)pyridin-2-yl)prop-2-ynyl)carbamate

HRID 626170Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[CH3:23][N:24]([CH2:32][C:33]#[CH:34])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28]>C(N(CC)CC)C>[CH3:23][N:24]([CH2:32][C:33]#[C:34][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:9])[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)=[CH:12][CH:11]=2)=[CH:6][N:7]=1)[C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:30])[CH3:28]

Participants

Conditions

Temperature: 80 °C

Procedure

A 25 mL Schlenk flask was charged with (6-chloropyridin-3-yl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanone (318 mg, 1.0 mmol), tetrakis(triphenylphos-phine)Palladium(0) (116 mg, 0.1 mmol, 10 mol %), cuprous iodide (38 g, 0.2 mmol, 20 mol %), triethylamine (5 mL), and tert-butyl methyl(prop-2-ynyl)carbamate (169 mg, 1 mmol). The flask was flushed with nitrogen three times and the mixture was stirred at 80° C. for 2 h. The solvent was evaporated under vacuum and the residue was purified by column chromatography to afford the desired product as yellow solid (180 mg, 40% yield).

Workup

customThe flask was flushed with nitrogen three times
customThe solvent was evaporated under vacuum
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-3dd706ccc56a426c88aaf370be75280c
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309211B2

Reaction notes

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