Potassium Carbonate → 6-Cyclopropyl-[3,4']bipyridinyl-2'-carboxylic acid (3-[1,3,4]oxadiazol-2-yl-phenyl)-amide

HRID 2178606Notes

Reaction equation

HRID 2178606 reaction equation
[O:1]1[CH:5]=[N:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:21])[C:14]2[CH:19]=[C:18](Br)[CH:17]=[CH:16][N:15]=2)[CH:9]=[CH:10][CH:11]=1.[CH:22]1([C:25]2[CH:30]=[CH:29][C:28](B3OC(C)(C)C(C)(C)O3)=[CH:27][N:26]=2)[CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[O:1]1[CH:5]=[N:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([NH:12][C:13]([C:14]2[CH:19]=[C:18]([C:28]3[CH:27]=[N:26][C:25]([CH:22]4[CH2:24][CH2:23]4)=[CH:30][CH:29]=3)[CH:17]=[CH:16][N:15]=2)=[O:21])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 457864292-Cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 58102932N-(3-(1,3,4-oxadiazol-2-yl)phenyl)-4-bromopicolinamide

Product 1

HCID 581029196-Cyclopropyl-[3,4']bipyridinyl-2'-carboxylic acid (3-[1,3,4]oxadiazol-2-yl-phenyl)-amideYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of N-(3-(1,3,4-oxadiazol-2-yl)phenyl)-4-bromopicolinamide (3.0 g, 8.7 mmol), 2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (2.25 g, 9.2 mmol), dppf(Pd)Cl2 (320 mg, 5 mol %), potassium carbonate (2.4 g, 17 mmol) in degassed toluene (10 mL), degassed water (10 mL) and degassed isopropanol (10 mL) was heated at 85° C. for 4 hours. The solvent was removed under reduced pressure and the residue was suspended and sonicated in methanol (40 mL) before being filtered and washed with methanol (10 mL). The grey powder was then suspended and sonicated in water (40 mL) before being filtered and washed with water (10 mL), methanol (10 mL) and diethyl ether (10 mL) to give 6-cyclopropyl-[3,4′]bipyridinyl-2′-carboxylic acid (3-[1,3,4]oxadiazol-2-yl-phenyl)-amide (3.0 g, 90%). 384.1 (M+1).

Workup

  1. customdegassed water (10 mL)
  2. customdegassed isopropanol (10 mL)
  3. customThe solvent was removed under reduced pressure
  4. customsonicated in methanol (40 mL)
  5. filtrationbefore being filtered
  6. washwashed with methanol (10 mL)
  7. customsonicated in water (40 mL)
  8. filtrationbefore being filtered
  9. washwashed with water (10 mL), methanol (10 mL) and diethyl ether (10 mL)

Sources & evidence

ORD record
ord-56f3ae2f6c4e424f903884f083014d08
Source dataset
uspto-grants-2015_06
Patent number
US09067933B2

Reaction notes

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