Toluene → 1-((2-(trimethylsilyl)ethoxy)methyl)-6-vinylquinolin-2(1H)-one

HRID 77484Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:7](=[O:20])[CH:6]=[CH:5]2.C([O-])([O-])=O.[K+].[K+].[C:27]1(C)C=CC=C[CH:28]=1>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:17][Si:16]([CH3:19])([CH3:18])[CH2:15][CH2:14][O:13][CH2:12][N:8]1[C:9]2[C:4](=[CH:3][C:2]([CH:27]=[CH2:28])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]1=[O:20]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 6-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)quinolin-2(1H)-one (1 g, 2.82 mmol) in toluene (20 mL) and water (20.00 mL) were added trivinylboraxin (0.684 g, 4.23 mmol), K2CO3 (0.780 g, 5.64 mmol). The reaction mixture was purged with N2 for 15 min, then Tetrakis (0.652 g, 0.564 mmol) was added and the reaction mixture was heated to 110° C. for 12 h. The reaction mixture was concentrated and dissolved in ethyl acetate and washed with water. The organic layer was dried over anhydrous sodium sulfate, and concentrated to get the 1-((2-(trimethylsilyl)ethoxy)methyl)-6-vinylquinolin-2(1H)-one (0.8 g, 94%), used without further purification. LCMS (ES-API), RT: 2.17 m/z 302.2 (M+H).

Workup

customThe reaction mixture was purged with N2 for 15 min
concentrationThe reaction mixture was concentrated
dissolutiondissolved in ethyl acetate
washwashed with water
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-8417f1ae5bab4f508b110ce8dfa9728e
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841301B2

Reaction notes

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