Water → HCID 86710049, compound

HRID 1468272Notes

Reaction equation

HRID 1468272 reaction equation
Br[C:2]1[C:3]([C:14]#[N:15])=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH:11]([CH3:13])[CH3:12])[N:10]=2)[CH:7]=1.[CH3:16]B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:11]([C:9]1[N:10]=[C:5]2[CH:4]=[C:3]([C:14]#[N:15])[C:2]([CH3:16])=[CH:7][N:6]2[CH:8]=1)([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 139377Methylboronic AcidHCID 86710050HCID 86710050, compound

Product 1

HCID 86710049HCID 86710049, compoundYield 38.5%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

6-Bromo-2-isopropylimidazo[1,2-a]pyridine-7-carbonitrile (200 mg, 0.757 mmol) obtained in step 1 was dissolved in 1,4-dioxane-water (2/1) (1.5 mL), and the solution was stirred under heat and reflux for 3 hours after adding methylboronic acid (140 mg, 2.33 mmol), sodium carbonate (240 mg, 2.26 mmol), and [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (62.0 mg, 0.0759 mmol). The reaction mixture was allowed to cool to room temperature, and, after adding water, the mixture was filtered through a Presep (registered trademark; diatomaceous earth, granular type M, 4.5 g/25 mL). The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=98/2) to give 2-isopropyl-6-methyl-imidazo[1,2-a]pyridine-7-carbonitrile (58.0 mg, yield 38%).

Workup

  1. temperatureunder heat
  2. temperaturereflux for 3 hours
  3. filtrationthe mixture was filtered through a Presep (registered trademark; diatomaceous earth, granular type M, 4.5 g/25 mL)
  4. customThe solvent was then evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=98/2)

Sources & evidence

ORD record
ord-8cd0758c1b0a46c380341ade3ef4a997
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

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