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

HRID 1909470Notes

Reaction equation

HRID 1909470 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-745a2081353149b384cc1895e17cbc45
Source dataset
uspto-grants-2013_12
Patent number
US08598360B2

Reaction notes

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