Water → Butyl (2E)-3-[4-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-(methyloxy)-2-pyridinyl]-2-propenoate

HRID 15348

Reaction equation

HRID 15348 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH:5]=[C:4]([O:17][CH3:18])[N:3]=1.N(C)(C1CCCCC1)C1CCCCC1.[C:33]([O:37][CH2:38][CH2:39][CH2:40][CH3:41])(=[O:36])[CH:34]=[CH2:35].O>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.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]>[CH3:14][C:13]([Si:10]([CH3:12])([CH3:11])[O:9][CH2:8][C:6]1[CH:5]=[C:4]([O:17][CH3:18])[N:3]=[C:2](/[CH:35]=[CH:34]/[C:33]([O:37][CH2:38][CH2:39][CH2:40][CH3:41])=[O:36])[CH:7]=1)([CH3:16])[CH3:15]

Participants

8

Reactant 4

HCID 962WaterHCID 8846Butyl AcrylateHCID 24210N-Methyl dicyclohexylamineHCID 574868884-(((tert-Butyldimethylsilyl)oxy)methyl)-2-chloro-6-methoxypyridine

Product 1

HCID 57486889Butyl (2E)-3-[4-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-(methyloxy)-2-pyridinyl]-2-propenoateYield 68%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 178418851HCID 178418851, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 2-chloro-4-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-(methyloxy)pyridine (9.20 g, 32.01 mmol) in 1,4-dioxane (100 ml) was treated with Pd(Pt-Bu3)2 (327 mg, 0.64 mmol), Pd2(dba)3 (293 mg, 0.32 mmol), Cy2NMe (7.53 ml, 35.21 mmol) and n-butyl acrylate (5.96 ml, 41.62 mmol). The reaction was heated at 120° C. for 1 h and was then treated with water extracted 3× with diethyl ether, dried (magnesium sulphate), evaporated and chromatographed on silica gel (250 g), eluting with 1:4 ethyl acetate-hexane to give the desired product (8.25 g, 68%).

Workup

  1. extractionextracted 3× with diethyl ether
  2. dry with materialdried (magnesium sulphate)
  3. customevaporated
  4. customchromatographed on silica gel (250 g)
  5. washeluting with 1:4 ethyl acetate-hexane

Sources & evidence

ORD record
ord-b6a97985058d4259ad42a7b03ab67cf0
Source dataset
uspto-grants-2010_06
Patent number
US07732461B2

Linked notes

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