Sodium Hydroxide → HCID 22561761, compound

HRID 2191410Notes

Reaction equation

HRID 2191410 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][NH:13]3)O1.Br[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:21]=1[F:27].[OH-].[Na+]>O1CCCC1>[F:26][C:22]1[C:21]([F:27])=[CH:20][CH:25]=[CH:24][C:23]=1[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27332601-Bromo-2,3-difluorobenzeneHCID 113224711H-Indole-4-boronic acid, pinacol ester

Product 1

HCID 22561761HCID 22561761, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole 6b (1.22 g, 5 mmol) was dissolved in 20 ml of tetrahydrofuran under stirring, and added with 1-bromo-2,3-difluoro-benzene (0.97 g, 5 mmol), tetrakis (triphenylphosphine)palladium (0.17 g, 0.15 mmol) and sodium hydroxide solution (7 ml, 2 mol/L) under an argon atmosphere. Upon completion of the addition, the reaction system was stirred at 75° C. in an oil bath overnight. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was naturally cooled down to room temperature and extracted with ethyl acetate (20 ml×3). The combined organic extracts were washed with saturated brine (10 ml), dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 4-(2,3-difluoro-phenyl)-1H-indole 6c (800 mg, yield 70%) as a white solid.

Workup

  1. additionUpon completion of the addition
  2. stirringthe reaction system was stirred at 75° C. in an oil bath overnight
  3. extractionextracted with ethyl acetate (20 ml×3)
  4. washThe combined organic extracts were washed with saturated brine (10 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customto remove the drying agent
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d71cf85cd4054651a5144008aa07e511
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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