5-CHLORO-2,3-DIHYDRO-1H-INDEN-1-OL

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

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

Procedure: The title compound was prepared from 2-(5-hydroxy-1H-pyrazol-1-yl)pyridine-4-carbonitrile and 5-chloro-2,3-dihydro-1H-inden-1-ol according to the procedure for the preparation of Example 39, part C. 1H NMR (400 MHz, CDCl3): δ 2.36-2.44 (1H, m), 2.57-2.66 (1H, m), 2.90-2.98 (1H, m), 3.12-3.20 (1H, m), 5.73-5.75 (1H, m), 5.85 (1H, d, J=2.0 Hz), 7.20 (1H, d, J=8.0 Hz), 7.29 (1H, s), 7.32 (1H, d, J=8.0 Hz), 7.36 (1H, dd, J=1.8 Hz, 4.8 Hz), 7.63 (1H, d, J=2.0 Hz), 7.87 (1H, s), 8.65 (1H, d, J=4.8 Hz). [M+H] Calc'd for C18H13ClN4O, 337; Found, 337.

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2.5 g of 5-chloroindan-1-one and 30 ml of THF is cooled to 0-5° C., 2.5 ml of concentrated NaOH solution and then, in portions, 0.88 g of sodium borohydride are added and the reaction mixture is stirred overnight at RT. It is poured into 100 ml of water, the mixture is acidified to pH 2 by the addition of concentrated HCl solution, extracted with AcOEt, the organic phase is washed with saturated NaCl solution and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a cyclohexane/AcOEt mixture (80/20; v/v) to give 2.1 g of the expected product. extracted with AcOEt the organic phase is washed with saturated NaCl solution dried over Na2SO4 the solvent is evaporated off under vacuum The residue is chromatographed on silica using a cyclohexane/AcOEt mixture (80/20; v/v)

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

Procedure: The title compound was prepared from 2-(5-hydroxy-1H-pyrazol-1-yl)pyridine-4-carbonitrile and 5-chloro-2,3-dihydro-1H-inden-1-ol according to the procedure for the preparation of Example 39, part C. 1H NMR (400 MHz, CDCl3): δ 2.36-2.44 (1H, m), 2.57-2.66 (1H, m), 2.90-2.98 (1H, m), 3.12-3.20 (1H, m), 5.73-5.75 (1H, m), 5.85 (1H, d, J=2.0 Hz), 7.20 (1H, d, J=8.0 Hz), 7.29 (1H, s), 7.32 (1H, d, J=8.0 Hz), 7.36 (1H, dd, J=1.8 Hz, 4.8 Hz), 7.63 (1H, d, J=2.0 Hz), 7.87 (1H, s), 8.65 (1H, d, J=4.8 Hz). [M+H] Calc'd for C18H13ClN4O, 337. Found, 337.

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

Procedure: The title compound was prepared from 2-(5-hydroxy-1H-pyrazol-1-yl)pyridine-4-carbonitrile and 5-chloro-2,3-dihydro-1H-inden-1-ol according to the procedure for the preparation of Example 39, part C. 1H NMR (400 MHz, CDCl3): δ 2.36-2.44 (1H, m), 2.57-2.66 (1H, m), 2.90-2.98 (1H, m), 3.12-3.20 (1H, m), 5.73-5.75 (1H, m), 5.85 (1H, d, J=2.0 Hz), 7.20 (1H, d, J=8.0 Hz), 7.29 (1H, s), 7.32 (1H, d, J=8.0 Hz), 7.36 (1H, dd, J=1.8 Hz, 4.8 Hz), 7.63 (1H, d, J=2.0 Hz), 7.87 (1H, s), 8.65 (1H, d, J=4.8 Hz). [M+H] Calc'd for C18H13ClN4O, 337. Found, 337.

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

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a precooled (5–10° C.) solution of 5-chloro-indan-1-one (2.0 g, 12 mmoles) in 33 mL of anhydrous methanol was added sodium borohydride (0.43 g, 11 mmoles). The reaction mixture was stirred at 10° C. for 2 hrs and then at room temperature for 18 hrs. The reaction mixture was evaporated to afford a yellow residue. The residue was dissolved in 200 mL of diethyl ether and then washed with water (2×100 mL), with 0.10 N hydrochloric acid (2×100 mL), and then with brine (100 mL). The organic layer was separated, dried (sodium sulfate), filtered, and the filtrate was evaporated to provide the title compound in good purity. MS m/z 167 (M−1). at room temperature for 18 hrs The reaction mixture was evaporated to afford a yellow residue washed with water (2×100 mL), with 0.10 N hydrochloric acid (2×100 mL) The organic layer was separated dried (sodium sulfate) filtered the filtrate was evaporated

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

Procedure: The title compound was prepared from 2-(5-hydroxy-1H-pyrazol-1-yl)pyridine-4-carbonitrile and 5-chloro-2,3-dihydro-1H-inden-1-ol according to the procedure for the preparation of Example 39, part C. 1H NMR (400 MHz, CDCl3): δ 2.36-2.44 (1H, m), 2.57-2.66 (1H, m), 2.90-2.98 (1H, m), 3.12-3.20 (1H, m), 5.73-5.75 (1H, m), 5.85 (1H, d, J=2.0 Hz), 7.20 (1H, d, J=8.0 Hz), 7.29 (1H, s), 7.32 (1H, d, J=8.0 Hz), 7.36 (1H, dd, J=1.8 Hz, 4.8 Hz), 7.63 (1H, d, J=2.0 Hz), 7.87 (1H, s), 8.65 (1H, d, J=4.8 Hz). [M+H] Calc'd for C18H13ClN4O, 337; Found, 337.

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2.5 g of 5-chloroindan-1-one and 30 ml of THF is cooled to 0-5° C., 2.5 ml of concentrated NaOH solution and then, in portions, 0.88 g of sodium borohydride are added and the reaction mixture is stirred overnight at RT. It is poured into 100 ml of water, the mixture is acidified to pH 2 by the addition of concentrated HCl solution, extracted with AcOEt, the organic phase is washed with saturated NaCl solution and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a cyclohexane/AcOEt mixture (80/20; v/v) to give 2.1 g of the expected product. extracted with AcOEt the organic phase is washed with saturated NaCl solution dried over Na2SO4 the solvent is evaporated off under vacuum The residue is chromatographed on silica using a cyclohexane/AcOEt mixture (80/20; v/v)

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

Procedure: The title compound was prepared from 2-(5-hydroxy-1H-pyrazol-1-yl)pyridine-4-carbonitrile and 5-chloro-2,3-dihydro-1H-inden-1-ol according to the procedure for the preparation of Example 39, part C. 1H NMR (400 MHz, CDCl3): δ 2.36-2.44 (1H, m), 2.57-2.66 (1H, m), 2.90-2.98 (1H, m), 3.12-3.20 (1H, m), 5.73-5.75 (1H, m), 5.85 (1H, d, J=2.0 Hz), 7.20 (1H, d, J=8.0 Hz), 7.29 (1H, s), 7.32 (1H, d, J=8.0 Hz), 7.36 (1H, dd, J=1.8 Hz, 4.8 Hz), 7.63 (1H, d, J=2.0 Hz), 7.87 (1H, s), 8.65 (1H, d, J=4.8 Hz). [M+H] Calc'd for C18H13ClN4O, 337. Found, 337.