1,2-Dimethoxyethane → HCID 13764015, compound

HRID 572155Notes

Reaction equation

HRID 572155 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[C:13]2[N:14]([CH:18]=[CH:19][N:20]=2)[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>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>[N:20]1[CH:19]=[CH:18][N:14]2[CH:15]=[CH:16][CH:17]=[C:12]([C:5]3[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=3)[C:13]=12

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 177499338-Bromoimidazo[1,2-a]pyridine

Product 1

HCID 13764015HCID 13764015, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Procedure

A mixture of 4-hydroxyphenylboronic acid (0.77 g), 8-bromoimidazo[1,2-a]pyridine (1.1 g), tetrakis(triphenylphosphine)palladium(0) (0.19 g), sodium carbonate (2.1 g), DME (30 ml) and water (6 ml) was heated under reflux overnight under an argon atmosphere. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) and recrystallized from ethyl acetate to give the title compound (0.88 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight under an argon atmosphere
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-95b44ac2979c49c8af9e4cca615032c5
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Reaction notes

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