(3-Methoxy-1-propynyl)tributylstannane → 2-(3-Methoxyprop-1-ynyl)-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester

HRID 922055Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[C:6](Cl)=[N:7][C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:9][C:10]=1[CH3:11])=[O:4].C([Sn](CCCC)(CCCC)[C:24]#[C:25][CH2:26][O:27][CH3:28])CCC>O1CCOCC1.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>[CH3:1][O:2][C:3]([C:5]1[C:6]([C:24]#[C:25][CH2:26][O:27][CH3:28])=[N:7][C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:9][C:10]=1[CH3:11])=[O:4]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 700 mg (2.6 mmol) 2-chloro-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester and 1.39 g (3.9 mmol) tributyl(3-methoxyprop-1-ynyl)stannane in dioxane (10 ml) was added 273 mg (0.39 mmol) PdCl2(PPh3)2. Then the reaction solution was heated at 100° C. for 16 h. After cooling to RT the mixture was filtered through celite and the filtrate was concentrated in vacuo. The residue was dissolved in EtOAc and washed with water. The organic layer was dried over Na2SO4 and concentrated in vacuo. Purification of the residue by CC (5% KF-silica, hexane/EtOAc 19:1) provided 500 mg (1.64 mmol, 63%) 2-(3-methoxyprop-1-ynyl)-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester.

Workup

temperatureAfter cooling to RT the mixture
filtrationwas filtered through celite
concentrationthe filtrate was concentrated in vacuo
dissolutionThe residue was dissolved in EtOAc
washwashed with water
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated in vacuo
customPurification of the residue by CC (5% KF-silica, hexane/EtOAc 19:1)

Sources & evidence

ORD record: ord-d0e3f87a73614e2284a6ca500ff8af16
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278103B2

Reaction notes

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