3-Bromopyridine → HCID 13694122, compound

HRID 1826721Notes

Reaction equation

HRID 1826721 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-62fa0072f5c0403dad2d4f38686fd5db
Source dataset
uspto-grants-2006_05
Patent number
US07053086B2

Reaction notes

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