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

HRID 1040243
Notes
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Reaction equation

HRID 1040243 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 1140
Toluene
Solvent

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-dcd8fa55fae345adb362ba612d38c2ce
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08552196B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes