Potassium Carbonate → HCID 69487238, compound

HRID 498252Notes

Reaction equation

HRID 498252 reaction equation
CO[C:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH:6]=1)=[O:4].N1[CH:22]=[CH:21][C:20](B(O)O)=CC=1.BrC1C=[C:29](C=CN=1)[C:30]([OH:32])=[O:31].[C:36]([O-])([O-])=O.[K+].[K+]>CC#N.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.O>[C:21]([O:32][C:30](=[O:31])[CH2:29][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=2)[CH:6]=1)=[O:4])([CH3:20])([CH3:22])[CH3:36]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 2227012-Bromoisonicotinic acidHCID 2734379(Pyridin-4-yl)boronic acidHCID 46317480HCID 46317480, compound

Product 1

HCID 69487238HCID 69487238, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

The title compound was prepared from [2,4′]bipyridinyl-4-carboxylic acid methyl ester [prepared by the following procedure: A mixture of pyridine-4-boronic acid (0.7 g, 5.7 mmol), 2-bromo-isonicotinic acid (1.15 g, 5.7 mmol) and K2CO3 (0.63 g, 4.6 mmol) in CH3CN (120 ml)/H2O (10 ml) was degassed and Pd(PPh3)4 (0.13 g, 0.11 mmol) was added. The mixture was stirred for 24 h at 80° C. in an atmosphere of nitrogen and then concentrated in vacuum to a volume of about 10 ml. The pH was set to 6 by addition of 3N HCl and the solution was then evaporated in vacuum to dryness. The residue was stirred in 1N HCl-MeOH (23 ml) for 65 h at 50° C. The crude product was purified by chromatography (silica gel, AcOEt/cyclohexane 1:1) to give the methyl ester as light yellow oil (0.37 g).] (0.21 g, 1.0 mmol) by treatment with lithium tert-butyl acetate according to general procedure K (method b). Obtained as a light yellow oil (0.45 g, crude product).

Workup

  1. customprepared by the following procedure
  2. customwas degassed
  3. concentrationconcentrated in vacuum to a volume of about 10 ml
  4. additionThe pH was set to 6 by addition of 3N HCl
  5. customthe solution was then evaporated in vacuum to dryness
  6. stirringThe residue was stirred in 1N HCl-MeOH (23 ml) for 65 h at 50° C
  7. customThe crude product was purified by chromatography (silica gel, AcOEt/cyclohexane 1:1)

Sources & evidence

ORD record
ord-9b7cd606c66f4c9f9a3ef8eb3db82f98
Source dataset
uspto-grants-2005_09
Patent number
US06949542B2

Reaction notes

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