Ammonium Acetate → 2-(4-Benzo[1,3]dioxol-5-yl-2-methyl-oxazol-5-yl)-6-methyl-pyridine

HRID 917671Notes

Reaction equation

HRID 917671 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=O)[CH:11]([O:19][C:20](=O)[CH3:21])[C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.C([O-])(=O)C.[NH4+:28]>C(O)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[N:28]=[C:20]([CH3:21])[O:19][C:11]=3[C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 68886008Acetic acid 2-benzo[1,3]dioxol-5-yl-1-(6-methyl-pyridin-2-yl)-2-oxo-ethyl ester

Product 1

HCID 688842012-(4-Benzo[1,3]dioxol-5-yl-2-methyl-oxazol-5-yl)-6-methyl-pyridineYield 21%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of acetic acid 2-benzo[1,3]dioxol-5-yl-1-(6-methyl-pyridin-2-yl)-2-oxo-ethyl ester (80 mg, 0.26 mmol), ammonium acetate (200 mg, 2.6 mmol, 10 equiv) in acetic acid (4 mL) was heated to 105° C. for 3 hours. The resulting reaction mixture was concentrated in vacuo, and reverse phase high pressure liquid chromatography (a gradient from 5-30% acetonitrile in 0.1% aqueous formic acid) provided 2-(4-Benzo[1,3]dioxol-5-yl-2-methyl-oxazol-5-yl)-6-methyl-pyridine (15.9 mg, 21%).[LCMS: Rt=2.10 min; M+H=295.2]

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-60f8aa68289740b3973c5626b4f0fb7f
Source dataset
uspto-grants-2007_09
Patent number
US07273936B2

Reaction notes

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