2-bromo-2,3-dihydro-1H-indene

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

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

Procedure: To 2-indanol (Aldrich) (105 g, 0.78 mol) in pyridine (16 mL, 0.2 mol) and 340 mL of chloroform at -15° C. was added PBr3 (84 mL, 0.89 mol) over 45 min. The reaction mixture was stirred overnight at room temperature and extracted by addition of 450 mL of chloroform and 500 g of ice. The organic layer was washed twice with water, and dried over Na2SO4. The solvent was evaporated in vacuo, leaving a brown semi-solid. The product was distilled rapidly in vacuo and then fractionated to give 69 g (45%) 2-bromoindane, bp 90°-93°/3 mmHg; nD23 =1.5837. extracted by addition of 450 mL of chloroform and 500 g of ice The organic layer was washed twice with water dried over Na2SO4 The solvent was evaporated in vacuo leaving a brown semi-solid The product was distilled rapidly in vacuo

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

Procedure: To 2-indanol (Aldrich) (105 g, 0.78 mol) in pyridine (16 mL, 0.2 mol) and 340 mL of chloroform at -15 C. was added PBr3 (84 mL, 0.89 mol) over 45 min. The reaction mixture was stirred overnight at room temperature and extracted by addition of 450 mL of chloroform and 500 g of ice. The organic layer was washed twice with water, and dried over Na2SO4. The solvent was evaporated in vacuo, leaving a brown semi-solid. The product was distilled rapidly in vacuo and then fractionated to give 69 g (45%) 2-bromoindane, bp 90-93 /3 mmHg; nd23 =1.5837. extracted by addition of 450 mL of chloroform and 500 g of ice The organic layer was washed twice with water dried over Na2SO4 The solvent was evaporated in vacuo leaving a brown semi-solid The product was distilled rapidly in vacuo

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

Procedure: To 2-indanol (Aldrich) (105 g, 0.78 mol) in pyridine (16 mL, 0.2 mol) and 340 mL of chloroform at -15 C. was added PBr3 (84 mL, 0.89 mol) over 45 min. The reaction mixture was stirred overnight at room temperature and extracted by addition of 450 mL of chloroform and 500 g of ice. The organic layer was washed twice with water, and dried over Na2SO4. The solvent was evaporated in vacuo, leaving a brown semi-solid. The product was distilled rapidly in vacuo and then fractionated to give 69 g (45%) 2-bromoindane, bp 90-93 /3 mmHg; nd23 =1.5837. extracted by addition of 450 mL of chloroform and 500 g of ice The organic layer was washed twice with water dried over Na2SO4 The solvent was evaporated in vacuo leaving a brown semi-solid The product was distilled rapidly in vacuo

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

Procedure: Sodium ethoxide (40 gms) was stirred in 1 L of dimethyl sulfoxide until solution was complete. Then, 100 g of ethyl acetamido-cyanoacetate was added, and again stirred until solution was complete. 2-Bromoindane (101 g) was slowly added, using a few ml of DMSO to wash the container and addition funnel. The solution was stirred over a weekend. to wash the container and addition funnel The solution was stirred over a weekend

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

Procedure: Sodium ethoxide (40 gms) was stirred in 1 L of dimethyl sulfoxide until solution was complete. Then, 100 g of ethyl acetamido-cyanoacetate was added, and again stirred until solution was complete. 2-Bromoindane (101 g) was slowly added, using a few ml of DMSO to wash the container and addition funnel. The solution was stirred over a weekend. to wash the container and addition funnel The solution was stirred over a weekend

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 80 gms of 2-indanol in 200 ml of chloroform was added 12 ml of pyridine. The solution was cooled to 0° C. with an ice bath, and 64 ml of phosphorous tribromide slowly added over 30 minutes. The ice bath was removed, and the solution was refluxed for 1 hour, and let stand overnight. The ice bath was removed the solution was refluxed for 1 hour

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

Procedure: To 2-indanol (Aldrich) (105 g, 0.78 mol) in pyridine (16 mL, 0.2 mol) and 340 mL of chloroform at -15° C. was added PBr3 (84 mL, 0.89 mol) over 45 min. The reaction mixture was stirred overnight at room temperature and extracted by addition of 450 mL of chloroform and 500 g of ice. The organic layer was washed twice with water, and dried over Na2SO4. The solvent was evaporated in vacuo, leaving a brown semi-solid. The product was distilled rapidly in vacuo and then fractionated to give 69 g (45%) 2-bromoindane, bp 90°-93°/3 mmHg; nD23 =1.5837. extracted by addition of 450 mL of chloroform and 500 g of ice The organic layer was washed twice with water dried over Na2SO4 The solvent was evaporated in vacuo leaving a brown semi-solid The product was distilled rapidly in vacuo

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

Procedure: To 2-indanol (Aldrich) (105 g, 0.78 mol) in pyridine (16 mL, 0.2 mol) and 340 mL of chloroform at -15 C. was added PBr3 (84 mL, 0.89 mol) over 45 min. The reaction mixture was stirred overnight at room temperature and extracted by addition of 450 mL of chloroform and 500 g of ice. The organic layer was washed twice with water, and dried over Na2SO4. The solvent was evaporated in vacuo, leaving a brown semi-solid. The product was distilled rapidly in vacuo and then fractionated to give 69 g (45%) 2-bromoindane, bp 90-93 /3 mmHg; nd23 =1.5837. extracted by addition of 450 mL of chloroform and 500 g of ice The organic layer was washed twice with water dried over Na2SO4 The solvent was evaporated in vacuo leaving a brown semi-solid The product was distilled rapidly in vacuo

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 in 48% yield from methyl 2-(1H-imidazol-4-yl)pyridine-4-carboxylate (PREPARATION 5) and 2-bromo-2,3-dihydro-1H-indene according to the procedure for the preparation of Example 44, followed by saponification using NaOH in MeOH. 1HNMR (400 MHz, DMSO): δ 2.21 (2H, d), 3.52 (2H, d), 5.22 (1H, m), 7.23 (2H, m), 7.32 (2H, m), 7.45 (1H, t, J=5.4 Hz), 7.59 (1H, s), 7.82 (1H, s), 8.21 (1H, s), 8.35 (1H, d). [M+H] Calc'd for C18H15N3O2, 306. Found, 306.

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

Procedure: The title compound was prepared in 48% yield from methyl 2-(1H-imidazol-4-yl)pyridine-4-carboxylate (PREPARATION 5) and 2-bromo-2,3-dihydro-1H-indene according to the procedure for the preparation of Example 44, followed by saponification using NaOH in MeOH. 1HNMR (400 MHz, DMSO): δ 2.21 (2H, d), 3.52 (2H, d), 5.22 (1H, m), 7.23 (2H, m), 7.32 (2H, m), 7.45 (1H, t, J=5.4 Hz), 7.59 (1H, s), 7.82 (1H, s), 8.21 (1H, s), 8.35 (1H, d). [M+H] Calc'd for C18H15N3O2, 306. Found, 306.