Water → HCID 86710055, compound

HRID 1468274Notes

Reaction equation

HRID 1468274 reaction equation
Br[C:2]1[C:3]([C:22]#[N:23])=[CH:4][C:5]2[N:6]([C:8]([CH2:14][O:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[C:9]([CH:11]([CH3:13])[CH3:12])[N:10]=2)[CH:7]=1.[CH3:24]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:16]1([O:15][CH2:14][C:8]2[N:6]3[CH:7]=[C:2]([CH3:24])[C:3]([C:22]#[N:23])=[CH:4][C:5]3=[N:10][C:9]=2[CH:11]([CH3:13])[CH3:12])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 139377Methylboronic AcidHCID 86710056HCID 86710056, compound

Product 1

HCID 86710055HCID 86710055, compoundYield 62%

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-3-cyclohexyloxymethyl-2-isopropylimidazo[1,2-a]pyridine-7-carbonitrile (100 mg, 0.266 mmol) obtained in step 2 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 (64.0 mg, 1.07 mmol), sodium carbonate (85.0 mg, 0.802 mmol), and [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (44.0 mg, 0.0539 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 3-cyclohexyloxymethyl-2-isopropyl-6-methylimidazo[1,2-a]pyridine-7-carbonitrile (51.4 mg, yield 62%).

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-9520ea12ac1b484395e8115b68984c01
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

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