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

HRID 626173Notes

Reaction equation

I[C:2]1[CH: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]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.CCN(CC)CC>[CH3:23][N:24]([CH2:32][C:33]#[C:34][C:2]1[CH:7]=[CH:6][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:4][CH:3]=1)[C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:30])[CH3:28]

Participants

Conditions

Temperature: 90 °C

Procedure

A 25 mL Schlenk flask was charged with (4-iodophenyl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanone (408 mg, 1 mmol), Pd(PPh3)2Cl2 (18 mg, 0.025 mmol), CuI (10 mg, 0.05 mmol), Et3N (10 mL), and tert-butyl methyl(prop-2-ynyl)carbamate (255 mg, 1.5 mmol). The flask was flushed with argon three times and the mixture was stirred at 90° C. for 3 h. The solvent was evaporated under vacuum and the residue was purified by columnchromatography to give the desired product (270 mg, 60% yield).

Workup

customThe flask was flushed with argon three times
customThe solvent was evaporated under vacuum
customthe residue was purified by columnchromatography

Sources & evidence

ORD record: ord-d749bb4a42ce447382d5206556b974ee
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309211B2

Reaction notes

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