Sodium Hydroxide → HCID 22135435, compound

HRID 1826709Notes

Reaction equation

HRID 1826709 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.Cl.Br[C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1>[Pd].C1COCC1>[N:26]1[CH:27]=[CH:28][C:23]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][NH:15]3)=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 881004-Bromopyridinium chlorideHCID 113224711H-Indole-4-boronic acid, pinacol ester

Product 1

HCID 22135435HCID 22135435, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Palladium catalyst Pd(PPh3)4 (1.00 g, 0.87 mmol) and freshly prepared aqueous sodium hydroxide (4.63 g, 115.9 mmol in 42 mL water) were added to a mixture of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (7.03 g, 28.9 mmol) and 4-bromopyridine hydrochloride (5.68 g, 29.2 mmol) in THF (98 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 ethyl acetate (400 mL) added. The organic layer was isolated, washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was triturated with dichloromethane to give 5.1 g (91%) of 4-pyridin-4-yl-1H-indole.

Workup

  1. customThe system was degassed
  2. custompurged three times with nitrogen
  3. temperatureIt was then cooled to room temperature
  4. additionethyl acetate (400 mL) added
  5. customThe organic layer was isolated
  6. washwashed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customThe residue was triturated with dichloromethane

Sources & evidence

ORD record
ord-3e4ef83a1b7240baa2690d2e36e998c3
Source dataset
uspto-grants-2006_05
Patent number
US07053086B2

Reaction notes

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