1-bromo-4-(3-chloropropoxy)benzene

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

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

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

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

Procedure: To a mixture of 1-bromo-4-(3-chloropropoxy)benzene (1.25 g) and tetrakistriphenylphosphinepalladium (58 mg) in toluene (12 mL) and potassium carbonate (2.07 g) in water (6 mL) is added pyridine-4-boronic acid (380 mg) dissolved in ethanol. The mixture is heated for five hours at a temperature close to 80° C. Solvents are removed under reduced pressure and the residue dissolved in ethyl acetate. The organic phase is washed with a 10% aqueous solution of potassium hydroxide, then with water, dried over magnesium sulfate, filtered and concentrated. The residue is purified by chromatography over silica gel (eluent dichloromethane/methanol from 100/0 to 95/5) to give 408 mg of 4-(4-(3-chloropropoxy)phenyl]pyridine as an ochre oil used without further purification. The mixture is heated for five hours at a temperature close to 80° C Solvents are removed under reduced pressure the residue dissolved in ethyl acetate The organic phase is washed with a 10% aqueous solution of potassium hydroxide with water, dried over magnesium sulfate filtered concentrated The residue is purified by chromatography over silica gel (eluent dichloromethane/methanol from 100/0 to 95/5)

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

Procedure: Following the procedure described in example 24, but starting from 1-bromo-4-(3-chloropropoxy)benzene (2.5 g), potassium carbonate (4.14 g), 4-pyridylboronic acid (1.47 g) and palladium tetrakistriphenylphosphine (116 mg) in toluene (24 mL) affords 2.11 g of 4-[4-(3-chloropropoxy)phenyl]pyridine as a white solid.

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

Procedure: Following the procedure described in example 24, but starting from 1-bromo-4-(3-chloropropoxy)benzene (2.5 g), potassium carbonate (4.14 g), 4-pyridylboronic acid (1.47 g) and palladium tetrakistriphenylphosphine (116 mg) in toluene (24 mL) affords 2.11 g of 4-[4-(3-chloropropoxy)phenyl]pyridine as a white solid.

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

Procedure: 4-Bromophenol was reacted with 2-chloropropyl-p-toluenesulfonate and Cs2CO3 to give 1-bromo-4-(3-chloropropoxy)benzene.

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

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

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

Procedure: Prepared by Procedure G and Scheme B1 using 1-bromo-4-(3-chloropropoxy)benzene and 2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide: 1H NMR (400 MHz, CDCl3) δ 7.51 (s, 1H), 7.37 (d, 2H, J=7.6 Hz), 7.26 (m, 3H), 6.97 (d, 1H, J=7.7 Hz), 6.79 (d, 2H, J=7.7 Hz), 4.01 (t, 2H, J=5.6 Hz), 3.08 (d, 2H, J=9.4 Hz), 2.53 (m, 4H), 2.05 (m, 4H), 1.84 (m, 4H), 1.24 (d, 6H, J=5.9 Hz); Anal. Calcd for C24H31BrN2O2.HCl+0.34CHCl3: C, 54.5; H, 6.08; N, 5.22. Found: C, 54.5; H, 6.22; N, 5.22; ESMS m/e: 459.1 (M+H)+. Prepared by Procedure G and Scheme B1

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

Procedure: Prepared by Procedure U and Scheme AK using 4-bromophenol and 1-bromo-3-chloropropane. Prepared by Procedure U and Scheme AK

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

Procedure: Prepared by Procedure G and Scheme B1 using 1-bromo-4-(3-chloropropoxy)benzene and 2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide: 1H NMR (400 MHz, CDCl3) δ 7.51 (s, 1H), 7.37 (d, 2H, J=7.6 Hz), 7.26 (m, 3H) 6.97 (d, 1H, J=7.7 Hz), 6.79 (d, 2H, J=7.7 Hz), 4.01 (t, 2H, J=5.6 Hz), 3.08 (d, 2H, J=9.4 Hz), 2.53 (m, 4H), 2.05 (m, 4H), 1.84 (m, 4H), 1.24 (d, 6H, J=5.9 Hz); Anal. Calcd for C24H31BrN2O2.HCl+0.34CHCl3: C, 54.5; H, 6.08; N, 5.22. Found: C, 54.5; H, 6.22; N, 5.22; ESMS m/e: 459.1 (M+H)+. Prepared by Procedure G and Scheme B1