1,2-Dimethoxyethane → HCID 86674312, compound

HRID 509612Notes

Reaction equation

HRID 509612 reaction equation
Br[C:2]1[N:3]=[C:4]([CH:8]=[O:9])[N:5]([CH3:7])[CH:6]=1.[O:10]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11]1.COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>[Cl-].[Na+].O.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.C1COCC1>[O:10]1[CH:14]=[CH:13][C:12]([C:2]2[N:3]=[C:4]([CH:8]=[O:9])[N:5]([CH3:7])[CH:6]=2)=[CH:11]1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acidHCID 127422794-broMo-1-Methyl-1H-iMidazole-2-carbaldehyde

Product 1

HCID 86674312HCID 86674312, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
120 °C

Procedure

A glass vial was charged with 4-bromo-1-methyl-1H-imidazole-2-carbaldehyde (567 mg, 3.0 mmol), furan-3-boronic acid (504 mg, 4.5 mmol), 1,2-dimetoxyethane (12 mL) and 1M sodium carbonate solution (4.5 mL). The slurry was deoxygenated by bubbling argon through then tetrakis(triphenylphosphine)palladium(0) (78 mg, 0.0675 mmol) was added and the vessel sealed and warmed to 120° C. and stirred at this temperature for 5 hours, then 110° C. for 12 hours. THF (45 mL) was added to the cooled mixture followed by brine (15 mL). The organic layer was separated and the aqueous extracted with EtOAc (2×50 mL). The combined extracts were dried over Na2SO4, filtered and the volatiles removed in vacuo. The residue was purified by column chromatography on silica gel (Gradient: n-heptane/EtOAc=3/1 to n-heptane/EtOAc=1/1) to yield the title compound (326 mg, 62%) as a yellow solid.

Workup

  1. customThe slurry was deoxygenated
  2. additionwas added
  3. customthe vessel sealed
  4. wait110° C. for 12 hours
  5. customThe organic layer was separated
  6. extractionthe aqueous extracted with EtOAc (2×50 mL)
  7. dry with materialThe combined extracts were dried over Na2SO4
  8. filtrationfiltered
  9. customthe volatiles removed in vacuo
  10. customThe residue was purified by column chromatography on silica gel (Gradient: n-heptane/EtOAc=3/1 to n-heptane/EtOAc=1/1)

Sources & evidence

ORD record
ord-77ca9b8b7c2b485db8bcc7ebacd6b646
Source dataset
uspto-grants-2015_08
Patent number
US09096589B2

Reaction notes

Loading…