Water → HCID 11052319, compound

HRID 571599Notes

Reaction equation

HRID 571599 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].O.[CH:16](O)([CH3:18])[CH3:17]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].CCOCC>[CH3:8][C:5]1[N:6]=[CH:7][C:2]([C:17]2[CH:7]=[N:6][C:5]([CH3:4])=[CH:18][CH:16]=2)=[CH:3][CH:4]=1

Participants

9

Reactant 4

HCID 962Water2×HCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 12010205-Bromo-2-methylpyridine

Product 1

HCID 11052319HCID 11052319, compoundYield 51.2%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 5-bromo-2-methyl-pyridine (1.37 g, 8 mmol), Pd(OAc)2 (90 mg, 0.4 mmol), K2CO3 (1.10 g, 8 mmol), tetra-n-butylammonium bromide (1.29 g, 4 mmol) in DMF (0.9 mL)/H2O (0.35 mL) was stirred at 115° C. under argon for 2 minutes. Isopropanol (480 mg, 8 mmol) was added. After stirring for 48 h, the reaction mixture was allowed to cool down to room temperature. The mixture was added water and ether, and the organic phase was separated, washed with brine, and dried over anhydrous Na2SO4. The solvent was then evaporated under reduced pressure and the residue was purified by silica gel column chromatography to afford the desired product as white crystals (0.377 g, 51%): 1H NMR (500 MHz, C6D6) δ 8.71 (d, J=1.5 Hz, 2H), 7.18 (dd, J=8.0 Hz, 2.5 Hz, 2H), 6.66 (d, J=8.0 Hz, 2H), 2.45 (s, 6H).

Workup

  1. stirringAfter stirring for 48 h
  2. temperatureto cool down to room temperature
  3. customthe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was then evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ac23e4815349401ebcde403ab48df35a
Source dataset
uspto-grants-2015_05
Patent number
US09029332B2

Reaction notes

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