7-Bromo-1-benzofuran → HCID 69021207, compound

HRID 1865086Notes

Reaction equation

HRID 1865086 reaction equation
Br[C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[K+].B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.[CH2:34]([O:36][C:37]([C:39]1[N:40]([CH3:62])[C:41](CC)=[C:42]([C:58]#[N:59])[C:43]=1[C:44]1[CH:49]=[CH:48][C:47](OS(C(F)(F)F)(=O)=O)=[CH:46][CH:45]=1)=[O:38])[CH3:35].C(=O)([O-])[O-].[Na+].[Na+].O>CN(C=O)C.O>[CH2:34]([O:36][C:37]([C:39]1[N:40]([CH3:62])[CH:41]=[C:42]([C:58]#[N:59])[C:43]=1[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[C:7]1[CH:6]=[CH:5][C:4]2[C:8]=1[O:9][CH:10]=[CH:2][CH:3]=2)=[O:38])[CH3:35]

Participants

8

Reactant 5

HCID 1136287-Bromo-1-benzofuranHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 2735133Sodium Carbonate MonohydrateHCID 57974728HCID 57974728, compound

Product 1

HCID 69021207HCID 69021207, compoundYield 49.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Add together 7-bromo-benzofuran (300 mg, 1.50 mmol), potassium acetate (431 mg, 2 Eq.), and bis(pinacolato)diboron (390 mg, 1.6 Eq.) in DMF (30 mL) and stir for 10 minutes while degassing with nitrogen. Add [11′bis(diphenylphosphino) ferrocene]dichloro-palladium(II) (30 mg) to the reaction mixture and stir at 80° C. for 2 hours under a nitrogen atmosphere. Cool mixture to room temperature and add 4-cyano-5-ethyl-1-methyl-3-(4-trifluoromethanesulfonyloxyphenyl)-1H-pyrrole-2-carboxylic acid ethyl ester (prepared in example E-97a or E-97b) (1.3 g, 2 Eq.), 2.0M sodium carbonate/water (3.6 mL ), and [11′bis(diphenylphosphino)ferrocene]dichloro-palladium(II) (30 mg) to the mixture and heat at 80° C. overnight. Cool to room temperature and pour into water and extract the desired product into ethyl acetate. Separate layers, and wash the organic layer once with water, dry over potassium carbonate, filter, and concentrate under reduced vacuum to give 1.08 g as a dark solid. Purify the material by silica gel chromatography (Chromatotron™) eluting with hexane/ethyl acetate 7:3 to provide 275 mg of the title compound as a white solid. Mass spectrum (m/e): 399.2 (M*+1).

Workup

  1. customwhile degassing with nitrogen
  2. stirringAdd [11′bis(diphenylphosphino) ferrocene]dichloro-palladium(II) (30 mg) to the reaction mixture and stir at 80° C. for 2 hours under a nitrogen atmosphere
  3. temperatureheat at 80° C. overnight
  4. temperatureCool to room temperature
  5. extractionextract the desired product into ethyl acetate
  6. washSeparate layers, and wash the organic layer once with water
  7. dry with materialdry over potassium carbonate
  8. filtrationfilter
  9. concentrationconcentrate under reduced vacuum
  10. customto give 1.08 g as a dark solid
  11. customPurify the material by silica gel chromatography (Chromatotron™)
  12. washeluting with hexane/ethyl acetate 7:3

Sources & evidence

ORD record
ord-c47302b84f7c49a1bda8da84ee7a9248
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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