Reaktion #219399

ord-20ae7364aea64bc39f849fc707d69485

Reaktionsgleichung

CC(C)(C)C(=O)Cl
pivaloyl chloride
CCN(CC)CC
Triethlyamine
Nc1ncccc1C=O
2-aminopyridine-3-carboxaldehyde
CC(C)(C)C(=O)Nc1ncccc1C=O
title compound
Ausbeute 90.0%
CC(C)(C)C(=O)Nc1ncccc1C=O
N-(3-Formylpyridin-2-yl)pivalamide
Ausbeute 90.0%

Reaktionsbedingungen

Temperatur
0°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeReaction
  2. 2
    Temperaturwas warmed to room temperature
  3. 3
    WaschenMixture was washed successively with water (2×50 mL) and brine (30 mL)
  4. 4
    TrocknenOrganic layer was dried (magnesium sulfate)
  5. 5
    Filtrationfiltered
  6. 6
    Einengenconcentrated in vacuo

Vorschrift

Triethlyamine (7.6 mL, 54 mmol), was added to a solution of 2-aminopyridine-3-carboxaldehyde (4.45 g, 36 mmol) in dichloromethane (70 mL). Mixture was cooled to 0° C. A solution of pivaloyl chloride (5.3 mL, 43 mmol) in dichloromethane (30 mL) was added to the mixture. Reaction was warmed to room temperature. Mixture stirred at room temperature for 63 hours. Mixture was washed successively with water (2×50 mL) and brine (30 mL). Organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Silica gel chromatography afforded the title compound as off-white solid in 90% yield. (M+H)+=207.1.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07384930B2uspto-grants-2008_06