2,4,6-Trivinylboroxin-Pyridine Complex → HCID 66933582, compound

HRID 1908760Notes

Reaction equation

HRID 1908760 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([O:8][CH:9]([CH3:11])[CH3:10])=[N:6][CH:7]=1.B1(C=C)OB([CH:19]=[CH2:20])OB(C=C)O1.C1C=CN=CC=1>COCCOC.C([O-])([O-])=O.[K+].[K+].CCOCC.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>[CH:9]([O:8][C:5]1[C:4]([CH3:12])=[CH:3][C:2]([CH:19]=[CH2:20])=[CH:7][N:6]=1)([CH3:11])[CH3:10]

Participants

7

Reactant 2

HCID 27348062,4,6-Trivinylboroxin-Pyridine ComplexHCID 225911775-Bromo-3-methyl-2-[(propan-2-yl)oxy]pyridine

Product 1

HCID 66933582HCID 66933582, compoundYield 75.4%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 5-bromo-2-isopropoxy-3-methyl-pyridine (1.24 g, 5.39 mmol) and 2,4,6-trivinylcyclotriboroxane pyridine complex (1.27 g, 5.26 mmol) in DME (12 mL) and 2 M aq. K2CO3 (5 mL) is degassed and put under argon before Pd(PPh3)4 (112 mg, 0.097 mmol) is added. The mixture is stirred at 80° C. for 15 h before it is cooled to rt, diluted with ether (50 mL), washed with sat. aq. NaHCO3 solution (2×30 mL), dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 9:1 to give 2-isopropoxy-3-methyl-5-vinyl-pyridine (703 mg) as pale yellow oil; LC-MS: tR=1.01 min; [M+1]+=178.11.

Workup

  1. additionis added
  2. temperatureis cooled to rt
  3. washwashed with sat. aq. NaHCO3 solution (2×30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by CC on silica gel eluting with heptane:EA 9:1

Sources & evidence

ORD record
ord-84e41ab838c5433fac864a53803f0e4c
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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