Sodium Carbonate → HCID 68721785, compound

HRID 869921Notes

Reaction equation

HRID 869921 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH2:13][CH2:12]2)=[O:10])[CH:5]=[CH:4][C:3]=1[CH3:22].[CH3:23][O:24][C:25]1[CH:30]=[C:29](B(O)O)[CH:28]=[CH:27][N:26]=1.C(=O)([O-])[O-].[Na+].[Na+].B(O)O>COCCOC.[Pd].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:23][O:24][C:25]1[CH:30]=[C:29]([C:2]2[C:3]([CH3:22])=[CH:4][CH:5]=[C:6]([NH:8][C:9]([C:11]3([C:14]4[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=4)[CH2:13][CH2:12]3)=[O:10])[N:7]=2)[CH:28]=[CH:27][N:26]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 61668Boronic AcidHCID 23546919(2-Methoxypyridin-4-yl)boronic acidHCID 59165805HCID 59165805, compound

Product 1

HCID 68721785HCID 68721785, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

N-(6-Chloro-5-methylpyridin-2-yl)-1-(4-methoxyphenyl)cyclopropane carboxamide (63 mg, 0.20 mmol) was dissolved in 1,2-dimethoxyethane (2.0 mL) in a reaction tube. 2-Methoxypyridin-4-ylboronic acid (46 mg, 0.30 mmol), aqueous 2 M sodium carbonate (0.20 mL), and (Ph3P)4Pd (12 mg, 0.010 mmol) were added and the reaction mixture was heated at 80° C. under N2 atmosphere for 18 hours. Since the reaction was incomplete, it was re-treated with same amount of boronic acid, base and Pd catalyst and heated at 80° C. for 18 hours. The resulting material was cooled to room temperature, filtered, and evaporated under reduced pressure. The crude product was dissolved in DMSO (2 mL), filtered, and purified by reverse phase preparative HPLC to yield N-(2′-methoxy-3-methyl-2,4′-bipyridin-6-yl)-1-(4-methoxyphenyl)cyclopropane carboxamide. ESI-MS m/z calc. 389.2. found 390.5 (M+1)+. Retention time 1.84 minutes.

Workup

  1. temperatureheated at 80° C. for 18 hours
  2. temperatureThe resulting material was cooled to room temperature
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. dissolutionThe crude product was dissolved in DMSO (2 mL)
  6. filtrationfiltered
  7. custompurified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-1f1369ba88554a669915bf2104ddd1c5
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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