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1,2-Dimethoxyethane → HCID 44481757, compound

HRID 452719
Notes
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Reaction equation

HRID 452719 reaction equation
Br[C:2]1[C:6]2[CH:7]=[C:8]([C:11]3[O:12][C:13]([CH3:16])=[N:14][N:15]=3)[CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>C(OCC)(=O)C.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>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[C:6]3[CH:7]=[C:8]([C:11]4[O:12][C:13]([CH3:16])=[N:14][N:15]=4)[CH:9]=[CH:10][C:5]=3[O:4][CH:3]=2)=[CH:20][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 444806972-(3-Bromo-1-benzofuran-5-yl)-5-methyl-1,3,4-oxadiazole

Product 1

HCID 44481757HCID 44481757, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(3-bromo-1-benzofuran-5-yl)-5-methyl-1,3,4-oxadiazole (251 mg, 0.900 mmol), (4-fluorophenyl)boronic acid (140 mg, 1.00 mmol), tetrakis(triphenylphosphine)palladium(0) (31.2 mg, 0.0270 mmol), sodium carbonate (212 mg, 2.00 mmol), 1,2-dimethoxyethane (5 mL) and water (1 mL) was heated overnight under reflux under an argon atmosphere. After cooling, the reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) and recrystallized from hexane/ethyl acetate to give the title compound (182 mg, yield 69%) as colorless crystals.

Workup

  1. temperaturewas heated overnight
  2. temperatureunder reflux under an argon atmosphere
  3. temperatureAfter cooling
  4. washwashed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)
  8. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-055a91e051db4e8ca418c99394e771e7
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492378B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes