3-Bromopyridine → HCID 13694122, compound

HRID 988140Notes

Reaction equation

HRID 988140 reaction equation
[OH-].[Na+].CC1(C)C(C)(C)OB([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][NH:15]3)O1.Br[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1>[Pd].C1COCC1>[N:24]1[CH:25]=[CH:26][CH:27]=[C:22]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][NH:15]3)[CH:23]=1

Participants

6

Reactant 3

HCID 122863-BromopyridineHCID 14798Sodium HydroxideHCID 113224711H-Indole-4-boronic acid, pinacol ester

Product 1

HCID 13694122HCID 13694122, compoundYield 62.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Palladium catalyst Pd(PPh3)4 (284 mg, 0.25 mmol) and freshly prepared aqueous sodium hydroxide (984 mg in 9 mL of water) were added to a mixture of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (2 g, 8.2 mmol) and 3-bromopyridine (0.8 mL, 8.3 mmol) in THF (28 mL). The system was degassed and then purged three times with nitrogen. The mixture was stirred under nitrogen at 70° C. in an oil bath for 6 hours. It was then cooled to room temperature and 400 ml ethyl acetate was added. The organic layer was isolated, washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was column chromatographed to give 1 g (62%) of 4-pyridin-3-yl-1H-indole as a white solid.

Workup

  1. customThe system was degassed
  2. custompurged three times with nitrogen
  3. temperatureIt was then cooled to room temperature
  4. addition400 ml ethyl acetate was added
  5. customThe organic layer was isolated
  6. washwashed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customchromatographed

Sources & evidence

ORD record
ord-70aaf6cb1de04fe0b6019ab2d5ccef03
Source dataset
uspto-grants-2003_10
Patent number
US06635640B2

Reaction notes

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