Diisopropylethylamine → HCID 59301328, compound

HRID 2236193Notes

Reaction equation

HRID 2236193 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][N:5]=1)([O-:3])=[O:2].[CH3:11][O:12][CH2:13][CH2:14][NH:15][CH3:16].C(N(C(C)C)CC)(C)C>CCO>[CH3:11][O:12][CH2:13][CH2:14][N:15]([CH3:16])[C:7]1[CH:6]=[N:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 300977(2-Methoxyethyl)(methyl)amineHCID 8176205-Bromo-2-nitropyridine

Product 1

HCID 59301328HCID 59301328, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2-nitro-5-bromopyridine (500 mg, 3.15 mmol) in EtOH (15 mL) was treated with methoxyethyl-N-methylamine (1.12 g, 12.6 mmol) and diisopropylethylamine (2.2 mL, 12.6 mmol). The resulting mixture was then heated in a sealed tube at 90° C. for 4 days then cooled and partitioned between EtOAc and water. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was chromatographed on a silica gel column with a 40-100% EtOAc in hexanes gradient to afford the product as a thick yellow oil that crystallized slowly upon standing (270 mg, 41% yield). HRMS m/z calcd for C9H13N3O3 [M+Na]+: 234.0849; Found: 234.0850.

Workup

  1. temperaturethen cooled
  2. custompartitioned between EtOAc and water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on a silica gel column with a 40-100% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-2d952bd451d7492c899da99e014a52de
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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