Ammonium Chloride → HCID 10355537, compound

HRID 917664Notes

Reaction equation

HRID 917664 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:14][CH:13]=[N:12][C:11]=3Br)=[CH:9][C:4]=2[O:3][CH2:2]1.[Cl-].[NH4+:17]>C1COCC1.C(OCC)(=O)C.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>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:14][CH:13]=[N:12][C:11]=3[C:8]3[CH:9]=[CH:4][CH:5]=[CH:6][N:17]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 688862155-Benzo[1,3]dioxol-5-yl-4-bromo-oxazole

Product 1

HCID 10355537HCID 10355537, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a degassed solution of 5-benzo[1,3]dioxol-5-yl-4-bromo-oxazole (50 mg, 0.19 mmol) and tetrakis(triphenylphosphine)palladium(0) (11 mg, 0.009 mmol, 0.05 equiv) in THF (2 mL) was added 2-zinc bromo -pyridine (1 mL, 0.5 M in THF, 0.500 mmol, 2.6 equiv). The resulting reaction mixture was heated to reflux overnight, cooled to ambient temperature, treated with saturated aqueous ammonium chloride, and diluted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride, dried over magnesium sulfate and concentrated in vacuo. Silica gel chromatography (50% ethyl acetate in hexane) provided 2-(5-Benzo[1,3]dioxol-5-yl-oxazol4-yl)-pyridine (22.7 mg, 46%). [LCMS: Rt=1.79 min, M+H=267.1]

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux overnight
  4. washThe organic layer was washed with saturated aqueous ammonium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fc98b395b4d84db0b2cd7e7d7ba30132
Source dataset
uspto-grants-2007_09
Patent number
US07273936B2

Reaction notes

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