Tributyl(prop-1-yn-1-yl)stannane → Rac-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone

HRID 514196

Reaction equation

Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:10](=[O:23])[CH:11]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:12][C:13]=2[O:14][CH3:15])=[C:4]([CH3:24])[CH:3]=1.[CH2:25]([Sn](CCCC)(CCCC)C#CC)[CH2:26][CH2:27]C>C1(C)C=CC=CC=1.O>[CH3:8][C:6]1[CH:7]=[C:2]([C:25]#[C:26][CH3:27])[CH:3]=[C:4]([CH3:24])[C:5]=1[C:9]1[C:10](=[O:23])[CH:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:12][C:13]=1[O:14][CH3:15]

Participants

Conditions

Temperature: 130 °C

Procedure

To a degassed solution of rac-2-(4-bromo-2,6-dimethylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone (1.0 g, 2.5 mmol) in toluene (10 ml) is added tributyl(1-propynyl)tin (1.55 ml, 5.18 mmol) and tetrakistriphenylphosphine palladium(0) (0.5 g, 0.5 mmol) under a nitrogen atmosphere. The reaction mixture is heated at 130°C. for 40 minutes under microwave irradiation, then diluted with distilled water (20 ml) and extracted with ethyl acetate (50 ml×2). The combined organic fractions are washed with distilled water, brine, dried over sodium sulfate, filtered and the filtrate concentrated in vacuo to afford rac-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone. This material is used directly in the next step without further purification.

Workup

extractionextracted with ethyl acetate (50 ml×2)
washThe combined organic fractions are washed with distilled water, brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record: ord-212927a76a1e43d39965226043a3e4b6
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09107415B2

Linked notes

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