2-Aminopyridine → HCID 68491240, compound

HRID 1992300Notes

Reaction equation

HRID 1992300 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([B:9]([OH:11])[OH:10])=[CH:5][CH:4]=1)=O.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18]>ClC(Cl)C>[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([B:9]([OH:11])[OH:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 68491240HCID 68491240, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 4-formylphenylboronic acid (1 g, 6.67 mmol) and 2-pyridinylamine (2.51 g, 26.7 mmol) in dichloroethane (25 mL) was stirred under argon at room temperature. To this mixture was added NaB(OAc)3 (1.84 g, 8.67 mmol). The reaction mixture was quenched with H2O after 3 h. The solvent was removed under reduced pressure and the residue was dissolved in EtOAc and washed with water. The organic layer was then dried and concentrated in vacuo. The crude product was then purified by column chromatography (gradient from 20% to 80% EtOAc/hexane) to give product as colorless liquid (0.39 g, 30%). HPLC/MS: (M+H)+ 229.1 m/z. Retention time (LC-MS)=4.54 min. 1H NMR (CD3OD): 7.90 (1H, d); 7.59 (2H, s); 7.43 (1H, m); 7.30(2H, d); 6.55 (2H, m); 4.47 (2H

Workup

  1. customThe reaction mixture was quenched with H2O after 3 h
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in EtOAc
  4. washwashed with water
  5. customThe organic layer was then dried
  6. concentrationconcentrated in vacuo
  7. customThe crude product was then purified by column chromatography (gradient from 20% to 80% EtOAc/hexane)

Sources & evidence

ORD record
ord-b7863c1377484c47834bee6c7fcab35c
Source dataset
uspto-grants-2010_01
Patent number
US07648986B2

Reaction notes

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