Ethyl (5-bromobenzofuran)-2-carboxylate → HCID 22396306, compound

HRID 1070386Notes

Reaction equation

HRID 1070386 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([O:12]CC)=[O:11])=[CH:7][C:6]=2[CH:15]=1.[Br-].[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Zn+]>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:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([OH:12])=[O:11])=[CH:7][C:6]=2[CH:15]=1

Participants

5

Reactant 2

HCID 735184Ethyl (5-bromobenzofuran)-2-carboxylateHCID 178418723HCID 178418723, compound

Product 1

HCID 22396306HCID 22396306, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 5-bromo-benzofuran-2-carboxylate (1.0 g, 3.8 mmol), (prepared as described herein in Preparation1), 2-pyridinyl zinc bromide (15 mL, 7.5 mmol), tetrakis(triphenylphosphine)palladium (0) (100 mg), was stirred under an argon atmosphere and heated to 60° C. overnight. The mixture was cooled, poured into water, extracted with ethyl acetate, washed with brine, dried (MgSO4), and evaporated. Purification by chromatography gave 770 mg of 5-pyridin-2yl-benzofuran-2-carboxylic acid.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customPurification by chromatography

Sources & evidence

ORD record
ord-5b202be2b5aa4a8396e2a136c8743822
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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