1,2-Dimethoxyethane → HCID 59135100, compound

HRID 1994538Notes

Reaction equation

HRID 1994538 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4](I)[N:3]=1.[C:11](B(O)O)([CH3:13])=[CH2:12].COCCOC.C([O-])([O-])=O.[Na+].[Na+]>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.CCO>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([C:11]([CH3:13])=[CH2:12])[N:3]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 10855372(Prop-1-en-2-yl)boronic acidHCID 110990402-Bromo-6-iodo-3-methoxypyridine

Product 1

HCID 59135100HCID 59135100, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

In a tube were placed 2-bromo-6-iodo-3-methoxypyridine (700 mg, 2.236 mmol), isopropenylboronic acid (212 mg, 2.460 mmol), DME (7.5 mL), EtOH (2.8 mL), and 1M aq. Na2CO3 (5.6 mL). The mixture was degassed with N2. Next, Pd(PPh3)4 (206 mg, 0.179 mmol) was added and the mixture was degassed again with N2. The tube was sealed and heated at 80° C. for 16 hours. The reaction was then cooled to room temperature, diluted with EtOAc (100 mL), and washed with saturated NaHCO3 and brine (50 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (0 to 15% EtOAc/hexanes) afforded 2-bromo-6-isopropenyl-3-methoxypyridine. Rf=0.38 (25% EtOAc/hexanes). LCMS=230.0 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.36 (d, J=8.5 Hz, 1H), 7.07 (d, J=9.4 Hz, 1H), 5.81 (s, 1H), 5.21 (s, 1H), 3.92 (s, 3H), 2.16 (s, 3H).

Workup

  1. customIn a tube were placed
  2. customThe mixture was degassed with N2
  3. customthe mixture was degassed again with N2
  4. customThe tube was sealed
  5. temperatureThe reaction was then cooled to room temperature
  6. additiondiluted with EtOAc (100 mL)
  7. washwashed with saturated NaHCO3 and brine (50 mL each)
  8. dry with materialThe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification of the residue by flash chromatography on silica gel (0 to 15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-090684ad60a246269b7e94140bd7e676
Source dataset
uspto-grants-2010_01
Patent number
US07652049B2

Reaction notes

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