Potassium Carbonate → HCID 86637552, compound

HRID 1632046Notes

Reaction equation

HRID 1632046 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:12][CH3:13])=[C:7](B(O)O)[CH:8]=1)=[O:2].I[C:15]1[CH:16]=[C:17]([C:21]2[O:22][CH:23]=[N:24][N:25]=2)[CH:18]=[CH:19][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>COCCOC.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:13][O:12][C:6]1[C:7]([C:19]2[CH:20]=[CH:15][CH:16]=[C:17]([C:21]3[O:22][CH:23]=[N:24][N:25]=3)[CH:18]=2)=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343675-Formyl-2-methoxyphenylboronic acidHCID 687970502-(3-Iodophenyl)-1,3,4-oxadiazole

Product 1

HCID 86637552HCID 86637552, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-formyl-2-methoxyphenyl boronic acid (414 mg, 2.29 mmol), the above product, 2-(3-iodo-phenyl)-[1,3,4]oxadiazole, (626 mg, 2.29 mmol), aqueous 2N K2CO3 (3.4 mL, 3 equivalents), Pd(PPh3)2Cl2 (50 mg, 0.068 mmol) in DME (15 mL) was stirred at room 80° C. for 7 hours. Reaction mixture was cooled to r.t., then it was diluted with ethyl acetate (45 mL) and washed with water, brine and dried over Na2SO4. After removal of solvent, 700 mg of crude was obtained. Purification by column chromatography gave 350 mg of the product (Yield: 55%).

Workup

  1. customReaction mixture
  2. washwashed with water, brine
  3. dry with materialdried over Na2SO4
  4. customAfter removal of solvent, 700 mg of crude
  5. customwas obtained
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-4cf9f447736e48388afe5f220bd5ced8
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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