2-Bromo-6-methylpyridine → 2-(5-Benzo[1,3]dioxol-5-yl-oxazol4-yl)-6-methyl-pyridine

HRID 917663Notes

Reaction equation

HRID 917663 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.Br[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[N:18]=1.C[Sn](C)(C)[Sn](C)(C)C>O1CCOCC1.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:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[N:18]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 3

HCID 792052-Bromo-6-methylpyridineHCID 688862155-Benzo[1,3]dioxol-5-yl-4-bromo-oxazoleHCID 178477788HCID 178477788, compound

Product 1

HCID 688849292-(5-Benzo[1,3]dioxol-5-yl-oxazol4-yl)-6-methyl-pyridineYield 70.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-benzo[1,3]dioxol-5-yl-4-bromo-oxazole (156 mg, 0.58 mmol), 2-bromo-6-methyl-pyridine (100 mg, 0.58 mmol, 1 equiv), 1,1,1,2,2,2-hexamethyl-distannane (190 mg, 0.58 mmol, 1 equiv) and tetrakis(triphenylphosphine)palladium(0) (67 mg, 0.058 mmol, 0.1 equiv) in 1,4-dioxane (6 mL) was heated to reflux overnight. The resulting reaction mixture was cooled to ambient temperature and concentrated in vacuo. Silica gel chromatography (gradient from hexane to 30% ethyl acetate in hexane) provided 2-(5-Benzo[1,3]dioxol-5-yl-oxazol4-yl)-6-methyl-pyridine (114 mg, 70%).[LCMS: Rt=1.79 min, M+H=281.2]

Workup

  1. temperatureto reflux overnight
  2. customThe resulting reaction mixture
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7a38ba64e70947d7b565996804d8d2ae
Source dataset
uspto-grants-2007_09
Patent number
US07273936B2

Reaction notes

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