Ethanol → HCID 86597234, compound

HRID 1793444Notes

Reaction equation

HRID 1793444 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9](Br)[N:8]=1)=[O:6].[CH3:14][O:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23].C(O)C.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[OH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:19]2[CH:18]=[CH:17][C:16]([O:15][CH3:14])=[C:21]([O:22][CH3:23])[CH:20]=2)[N:8]=1)=[O:6]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27347023,4-Dimethoxyphenylboronic acidHCID 23395706HCID 23395706, compound

Product 1

HCID 86597234HCID 86597234, compoundYield 69.5%

Reagents, catalysts & solvents 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A quantity of 0.25 g (1.0 mmoles, 1 eq) of 6-bromo-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide and 0.28 g (1.5 mmoles, 1.5 eq) of 3,4-dimethoxyphenyl boronic acid are added in 20 mL of ethylene glycol dimethyl ether with 2 ml of ethanol and 2 ml of 2 M Na2CO3. The mixture is purged with N2 for 20 minutes, and then 57 mg (0.05 mmoles, 0.05 eq) of Tris (dibenzylideneacetone)-dipalladium (0) is added. The reaction is heated at 80° C. for 6 hours. At that time there is no starting material shown on TLC. The reaction is filtered through Celite and the solvent is removed. The residue is taken in ethyl acetate, washed with brine, dried over Na2SO4 and concentrated to afford 6-(3,4-dimethoxy-phenyl)-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide as a yellowish oil (0.21 g, 69%), which is used in the next step without purification. Analysis: MS (LC-MS): Calculated for C16H18N2O4 302.33, found 303.39 (M+1).

Workup

  1. customThe mixture is purged with N2 for 20 minutes
  2. filtrationThe reaction is filtered through Celite
  3. customthe solvent is removed
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ccf46ede910d40369dee25ac8de4f6cf
Source dataset
uspto-grants-2006_07
Patent number
US07081458B2

Reaction notes

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