Methyl Acrylate → HCID 22050195, compound

HRID 1831970Notes

Reaction equation

HRID 1831970 reaction equation
[Br:1][C:2]1[C:3](=[O:19])[NH:4][C:5](C)=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13](F)=[CH:12][C:11]=1F.[F-].[Cs+].CO[Si](OC)(OC)OC.[C:31]([O:35][CH3:36])(=[O:34])[CH:32]=[CH2:33]>O1CCCC1>[CH2:9]([O:8][C:7]1[CH:6]=[CH:5][N:4]([CH2:33][CH2:32][C:31]([O:35][CH3:36])=[O:34])[C:3](=[O:19])[C:2]=1[Br:1])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 7294Methyl AcrylateHCID 12682TetramethoxysilaneHCID 25953Cesium fluorideHCID 220504293-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methylpyridin-2(1H)-one

Product 1

HCID 22050195HCID 22050195, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methylpyridin-2(1H)-one (5.00 g, 17.85 mmol) and cesium fluoride (0.27 g, 1.78 mmol) were suspended in tetrahydrofuran (50 mL) followed by dropwise addition of tetramethylortho silicate (2.70 g, 17.85 mmol) at room temperature. After stirring for 10 minutes at room temperature, methyl acrylate (2.00 g, 23.20 mmol) was added dropwise and the reaction stirred at room temperature for 48 hours. The reaction mixture was filtered through a pad of Celite®. The filtrate was concentrated and the resulting residue subjected to chromatography (silica gel, ethyl acetate with 10% methanol/hexanes) to afford a white solid (6.10 g, 93%). 1H NMR (400 MHz, CDCl3) δ 7.42 (d, J=7.65 Hz, 1H), 7.41-7.29 (m, 5H), 6.04 (d, J=7.65 Hz, 1H), 5.20 (s, 2H), 4.17 (t, J=5.91 Hz, 2H), 3.63 (s, 3H), 2.85 (t, J=5.91 Hz, 2H). ES-HRMS m/z 366.0350 (M+H C16H16BrNO4 requires 366.0335).

Workup

  1. stirringthe reaction stirred at room temperature for 48 hours
  2. filtrationThe reaction mixture was filtered through a pad of Celite®
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c05568444121457da07c25ab7664c7c1
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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