Reacción #425617

Ecuación de reacción

Water

potassium carbonate

[(2R)-6-bromo-2,3-dihydro-1,4-benzodioxin-2-yl]methanol

6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole

→

title compound

Rendimiento 141.9%

6-chloro-5-[(2R)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-1H-indole-3-carbaldehyde

Rendimiento 141.9%

Disolventes

methylene chloride

DMF

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe resulting mixture was stirred for 30 min. at 90° C. under N2
2. 2
   ExtracciónThe aqueous layer was extracted with methylene chloride (30 mL×3)
3. 3
   SecadoThe combined organic layer was dried over sodium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Otroevaporated

Procedimiento

A mixture of [(2R)-6-bromo-2,3-dihydro-1,4-benzodioxin-2-yl]methanol (0.54 g, 2.05 mmol) (which can be prepared as in Biorg. Med. Chem. 2007, 15, 4048.), 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (0.52 g, 4.06 mmol) in DMF (4 mL) and dioxane (4 mL) was stirred at room temperature for 30 min. under N2. Pd(dppf)Cl2 (100 mg, 0.137 mmol) and 2N potassium carbonate (10 mL, 20 mmol) was added. The resulting mixture was stirred for 30 min. at 90° C. under N2. TLC showed the reaction was complete. Water (50 mL) and methylene chloride (50 mL) was added. The aqueous layer was extracted with methylene chloride (30 mL×3). The combined organic layer was dried over sodium sulfate, filtered and evaporated to give the title compound (1 g) which was used in the next step without further purification.

Fuente