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

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. The resulting mixture was stirred for 30 min. at 90° C. under N2 The aqueous layer was extracted with methylene chloride (30 mL×3) The combined organic layer was dried over sodium sulfate filtered evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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 2 N 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. The resulting mixture was stirred for 30 min. at 90° C. under N2 The aqueous layer was extracted with methylene chloride (30 mL×3) The combined organic layer was dried over sodium sulfate filtered evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. The resulting mixture was stirred for 30 min. at 90° C. under N2 The aqueous layer was extracted with methylene chloride (30 mL×3) The combined organic layer was dried over sodium sulfate filtered evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. The resulting mixture was stirred for 30 min. at 90° C. under N2 The aqueous layer was extracted with methylene chloride (30 mL×3) The combined organic layer was dried over sodium sulfate filtered evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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 2 N 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. The resulting mixture was stirred for 30 min. at 90° C. under N2 The aqueous layer was extracted with methylene chloride (30 mL×3) The combined organic layer was dried over sodium sulfate filtered evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. The resulting mixture was stirred for 30 min. at 90° C. under N2 The aqueous layer was extracted with methylene chloride (30 mL×3) The combined organic layer was dried over sodium sulfate filtered evaporated