2-Bromopyridine → 2-(Pyridin-2-yl)oxazole

HRID 877395Notes

Reaction equation

HRID 877395 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[O:7][CH:8]=[CH:9][N:10]=1)CCC.Br[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1>O1CCOCC1.CCOC(C)=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>[N:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:6]1[O:7][CH:8]=[CH:9][N:10]=1

Participants

6

Reactant 2

HCID 79732-BromopyridineHCID 154861832-(Tri-n-butylstannyl)oxazole

Product 1

HCID 114577582-(Pyridin-2-yl)oxazoleYield 67%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

2-(Tributylstannyl)oxazole (1.00 g, 2.79 mmol), (Ph3P)4Pd (0.1 equiv), and 2-bromopyridine (2 equiv) were dissolved in anhydrous 1,4-dioxane (15 mL) and the mixture was warmed at reflux for 24 h under Ar. The mixture was diluted with EtOAc, washed with saturated aqueous NaCl and dried over Na2SO4. Evaporation in vacuo yielded the crude product that was purified by flash chromatography (SiO2, 10-60% EtOAc-hexanes) to yield the title compound (275 mg, 67%) as a light yellow oil: 1H NMR (CDCl3, 500 MHz) δ 8.63 (m, 1H), 8.04 (d, 1H, J=7.5 Hz), 7.73-7.70 (m, 2H), 7.26-7.22 (m, 2H); 13C NMR (CDCl3, 125 MHz) δ 161.0, 150.2, 146.4, 140.1, 137.3, 129.1, 125.0, 122.3.

Workup

  1. temperaturethe mixture was warmed
  2. temperatureat reflux for 24 h under Ar
  3. washwashed with saturated aqueous NaCl
  4. dry with materialdried over Na2SO4
  5. customEvaporation in vacuo
  6. customyielded the crude product that
  7. customwas purified by flash chromatography (SiO2, 10-60% EtOAc-hexanes)

Sources & evidence

ORD record
ord-48315f67d5344ce297303c83363dc7ff
Source dataset
uspto-grants-2015_03
Patent number
US08987312B2

Reaction notes

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