5-Bromopyridine-2-carboxamide → HCID 58149557, compound

HRID 1920082Notes

Reaction equation

HRID 1920082 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH2:10])=[O:9])=[N:6][CH:7]=1.[OH:11][CH:12](O)[C:13]([C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1)=[O:14]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH:12]([OH:11])[C:13]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)=[O:14])=[O:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 7351515-Bromopyridine-2-carboxamideHCID 5684550216208-20-1

Product 1

HCID 58149557HCID 58149557, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromopicolinamide 111 (0.588 g, 2.92 mmol) and 2,2-dihydroxy-1-(naphthalen-1-yl)ethanone 112 (1.20 g, 5.67 mmol) in dioxane (20 mL) were heated at 100° C. for 18 hours. The dioxane was removed under vacuum and the residue was dissolved in chloroform and methanol and concentrated onto silica gel. The material was purified by auto flash system (CH2Cl2 to 1% MeOH: CH2Cl2) to give 5-bromo-N-(1-hydroxy-2-(naphthalen-1-yl)-2-oxoethyl)picolinamide 113 as a tan solid (0.74 g, 66%).

Workup

  1. customThe dioxane was removed under vacuum
  2. dissolutionthe residue was dissolved in chloroform
  3. concentrationmethanol and concentrated onto silica gel
  4. customThe material was purified by auto flash system (CH2Cl2 to 1% MeOH: CH2Cl2)

Sources & evidence

ORD record
ord-1eeb2caaeeac4f419dd0e77c598cef4c
Source dataset
uspto-grants-2012_05
Patent number
US08168795B2

Reaction notes

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