2,4,6-Trivinylboroxin-Pyridine Complex → HCID 86657314, compound

HRID 1908822Notes

Reaction equation

HRID 1908822 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Br:10])[N:3]=1.B1(C=C)OB([CH:17]=[CH2:18])OB(C=C)O1.C1C=CN=CC=1>COCCOC.C([O-])([O-])=O.[K+].[K+].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>[Br:10][C:4]1[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=[C:2]([CH:17]=[CH2:18])[N:3]=1

Participants

7

Reactant 2

HCID 27348062,4,6-Trivinylboroxin-Pyridine ComplexHCID 109015692,6-Dibromo-4-methoxypyridine

Product 1

HCID 86657314HCID 86657314, compoundYield 159.3%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of 2,6-dibromo-4-methoxy-pyridine (5.90 g, 22.1 mmol) in DME (60 mL) and 2 M aq. K2CO3-solution (20 mL), 2,4,6-trivinylcyclotriboroxane pyridine complex (3.19 g, 13.2 mmol) is added and the mixture is degassed and put under N2 before Pd(PPh3)4 (460 mg, 0.398 mmol) is added. The mixture is stirred at 85° C. for 2 h before it is again cooled to rt, diluted with water and extracted with EA. The org. extract is dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 4:1 to give 2-bromo-4-methoxy-6-vinyl-pyridine (4.50 g) as a yellow solid; LC-MS: tR=0.90 min, [M+1]+=213.83.

Workup

  1. additionis added
  2. customthe mixture is degassed
  3. additionis added
  4. temperatureis again cooled to rt
  5. extractionextracted with EA
  6. extractionextract
  7. dry with materialis dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product is purified by CC on silica gel eluting with heptane:EA 4:1

Sources & evidence

ORD record
ord-77e03e6d70b34bc5b96249d50bb38314
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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