4,5-dibromofuran-2-carbaldehyde

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A degassed mixture of the product of Step 3 (6.6 g, 26.0 mmol), 1-methoxyimino-indan-5-boronic acid (5.3 g, 26.0 mmol) and potasium carbonate (28 g, 202 mmol) in ethylene glycol dimethyl ether (150 ml) and water (75 ml) was treated with bis(triphenylphosphine) palladium (II) chloride (1.05 g, 1.5 mmol), then heated under reflux for 6 hours. After cooling to room temperature, the mixture was filtered through celite and the filtrate diluted with water and ethyl acetate. The organic phase was separated, washed with water and brine, dried, concentrated in vacuo and the residue purified by silica gel chromatography eluting with dichloromethane to give the title compound (3.06 g, 35%); MS(ES+) m/e 334/336 [M+H]+. heated under reflux for 6 hours the mixture was filtered through celite the filtrate diluted with water and ethyl acetate The organic phase was separated washed with water and brine dried concentrated in vacuo the residue purified by silica gel chromatography eluting with dichloromethane

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

Procedure: A degassed mixture of the product of Step 3 (6.6 g, 26.0 mmol), 1-methoxyimino-indan-5-boronic acid (5.3 g, 26.0 mmol) and potasium carbonate (28 g, 202 mmol) in ethylene glycol dimethyl ether (150 ml) and water (75 ml) was treated with bis(triphenylphosphine) palladium (II) chloride (1.05 g, 1.5 mmol), then heated under reflux for 6 hours. After cooling to room temperature, the mixture was filtered through celite and the filtrate diluted with water and ethyl acetate. The organic phase was separated, washed with water and brine, dried, concentrated in vacuo and the residue purified by silica gel chromatography eluting with dichloromethane to give the title compound (3.06 g, 35%); MS(ES+) m/e 334/336 [M+H]+. heated under reflux for 6 hours the mixture was filtered through celite the filtrate diluted with water and ethyl acetate The organic phase was separated washed with water and brine dried concentrated in vacuo the residue purified by silica gel chromatography eluting with dichloromethane

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Diisobutylaluminum hydride (80 ml, 1M solution in toluene) was added to a solution of the product from Step 2 (20 g, 63.4 mmol) in tetrahydrofuran (160 ml) at −78° C. The mixture was stirred at −78° C. for 1.5 hours and was then quenched with a saturated aqueous solution of ammonium chloride (40 ml). The reaction was allowed to warm to room temperature, diluted with ethyl acetate and 5M hydrochloric acid (20 ml) and stirred for 30 minutes. The organic layer was separated, washed twice with water and then brine, dried and concentrated in vacuo to yield the title compound (12.9 g, 81%); 1H NMR (CDCl3) 9.52 (1H, s), 7.21 (1H, s). was then quenched with a saturated aqueous solution of ammonium chloride (40 ml) to warm to room temperature diluted with ethyl acetate and 5M hydrochloric acid (20 ml) stirred for 30 minutes The organic layer was separated washed twice with water brine, dried concentrated in vacuo

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Diisobutylaluminum hydride (80 ml, 1M solution in toluene) was added to a solution of the product from Step 2 (20 g, 63.4 mmol) in tetrahydrofuran (160 ml) at −78° C. The mixture was stirred at −78° C. for 1.5 hours and was then quenched with a saturated aqueous solution of ammonium chloride (40 ml). The reaction was allowed to warm to room temperature, diluted with ethyl acetate and 5M hydrochloric acid (20 ml) and stirred for 30 minutes. The organic layer was separated, washed twice with water and then brine, dried and concentrated in vacuo to yield the title compound (12.9 g, 81%); 1H NMR (CDCl3) 9.52 (1H, s), 7.21 (1H, s). was then quenched with a saturated aqueous solution of ammonium chloride (40 ml) to warm to room temperature diluted with ethyl acetate and 5M hydrochloric acid (20 ml) stirred for 30 minutes The organic layer was separated washed twice with water brine, dried concentrated in vacuo

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

Procedure: A degassed mixture of the product of Step 3 (6.6 g, 26.0 mmol), 1-methoxyimino-indan-5-boronic acid (5.3 g, 26.0 mmol) and potasium carbonate (28 g, 202 mmol) in ethylene glycol dimethyl ether (150 ml) and water (75 ml) was treated with bis(triphenylphosphine) palladium (II) chloride (1.05 g, 1.5 mmol), then heated under reflux for 6 hours. After cooling to room temperature, the mixture was filtered through celite and the filtrate diluted with water and ethyl acetate. The organic phase was separated, washed with water and brine, dried, concentrated in vacuo and the residue purified by silica gel chromatography eluting with dichloromethane to give the title compound (3.06 g, 35%); MS(ES+) m/e 334/336 [M+H]+. heated under reflux for 6 hours the mixture was filtered through celite the filtrate diluted with water and ethyl acetate The organic phase was separated washed with water and brine dried concentrated in vacuo the residue purified by silica gel chromatography eluting with dichloromethane

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Diisobutylaluminum hydride (80 ml, 1M solution in toluene) was added to a solution of the product from Step 2 (20 g, 63.4 mmol) in tetrahydrofuran (160 ml) at −78° C. The mixture was stirred at −78° C. for 1.5 hours and was then quenched with a saturated aqueous solution of ammonium chloride (40 ml). The reaction was allowed to warm to room temperature, diluted with ethyl acetate and 5M hydrochloric acid (20 ml) and stirred for 30 minutes. The organic layer was separated, washed twice with water and then brine, dried and concentrated in vacuo to yield the title compound (12.9 g, 81%); 1H NMR (CDCl3) 9.52 (1H, s), 7.21 (1H, s). was then quenched with a saturated aqueous solution of ammonium chloride (40 ml) to warm to room temperature diluted with ethyl acetate and 5M hydrochloric acid (20 ml) stirred for 30 minutes The organic layer was separated washed twice with water brine, dried concentrated in vacuo