Sodium Hydroxide → 4-thiazol-2-yl-1H-indole

HRID 1826713Notes

Reaction equation

HRID 1826713 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[S:23][CH:24]=[CH:25][N:26]=1>[Pd].C1COCC1>[S:23]1[CH:24]=[CH:25][N:26]=[C:22]1[C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[CH:14][NH:15]2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 764302-BromothiazoleHCID 113224711H-Indole-4-boronic acid, pinacol ester

Product 1

HCID 221354134-thiazol-2-yl-1H-indoleYield 42.5%

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 2-bromothiazole (809 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 with brine, dried over anhydrous Na2SO4 and concentrated. The residue was triturated with dichloromethane to give 350 mg (42%) of 4-thiazol-2-yl-1H-indole as a pale yellow 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 with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customThe residue was triturated with dichloromethane

Sources & evidence

ORD record
ord-89832677df464cc9bc708f1d90bb12a0
Source dataset
uspto-grants-2006_05
Patent number
US07053086B2

Reaction notes

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