Tributylvinyltin → 8-Methoxy-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)-4-vinylquinoline

HRID 1095697Notes

Reaction equation

I[C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:14]2[N:18]3[CH:19]=[CH:20][C:21]([O:23][CH2:24][CH2:25][O:26][CH3:27])=[CH:22][C:17]3=[N:16][CH:15]=2)[CH:3]=1.O1C=C[CH:30]=[C:29]1P(C1OC=CC=1)C1OC=CC=1.C([Sn](CCCC)(CCCC)C=C)CCC>CN1C(=O)CCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:13][O:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([C:14]1[N:18]3[CH:19]=[CH:20][C:21]([O:23][CH2:24][CH2:25][O:26][CH3:27])=[CH:22][C:17]3=[N:16][CH:15]=1)[CH:3]=[C:2]2[CH:29]=[CH2:30]

Participants

Conditions

Temperature: 80 °C

Procedure

To 4-iodo-8-methoxy-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinoline (898 mg, 1.89 mmol) in NMP (10 mL) was added Pd2dba3 (87 mg, 0.09 mmol), trifuran-2-ylphosphine (88 mg, 0.37 mmol) and tributyl(vinyl)stannane (659 mg, 2.1 mmol). The reaction flask was purged with N2 and the reaction was stirred at 80° C. for 2 hours. The crude mixture was diluted with EtOAc (30 mL) then washed with H2O, dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography (EtOAc/Hexane 8:1) affording the desired product (80%).

Workup

customThe reaction flask was purged with N2
additionThe crude mixture was diluted with EtOAc (30 mL)
washthen washed with H2O
dry with materialdried over Na2SO4
concentrationconcentrated
customThe residue was purified by flash column chromatography (EtOAc/Hexane 8:1)

Sources & evidence

ORD record: ord-83b37aef7fb040018485a38d04728365
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138181B2

Reaction notes

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