Sodium Hydroxide → 4-pyrimidin-5-yl-1H-indole

HRID 988134Notes

Reaction equation

HRID 988134 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]=[N:26][CH:27]=1>[Pd].C1COCC1>[N:24]1[CH:23]=[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:27]=[N:26][CH:25]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 783445-BromopyrimidineHCID 113224711H-Indole-4-boronic acid, pinacol ester

Product 1

HCID 221354894-pyrimidin-5-yl-1H-indoleYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Palladium catalyst Pd(PPh3)4 (142 mg, 0.12 mmol) and freshly prepared aqueous sodium hydroxide (493 mg, 12.33 mmol, in 6 mL of water) were added to a mixture of 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-indole (1 g, 4.11 mmol) and 5-bromopyrimidine (784 mg, 4.93 mmol) in THF (20 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 4 hours. It was then cooled to room temperature and ethyl acetate (300 mL) was added. The organic layer was isolated, washed by brine, dried over anhydrous Na2SO4 and concentrated. The residue was triturated with dichloromethane to give 570 mg (71%) of 4-pyrimidin-5-yl-1H-indole as a pale green solid.

Workup

  1. customThe system was degassed
  2. custompurged three times with nitrogen
  3. temperatureIt was then cooled to room temperature
  4. additionethyl acetate (300 mL) was added
  5. customThe organic layer was isolated
  6. washwashed by brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customThe residue was triturated with dichloromethane

Sources & evidence

ORD record
ord-13431cd501fa45f6962f9114eb9b3b30
Source dataset
uspto-grants-2003_10
Patent number
US06635640B2

Reaction notes

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