4-(2-methylphenyl)benzaldehyde

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

Procedure: 4-Chlorobenzaldehyde (144 mg, 1.02 mmol) reacted with 2-methylphenylboronic acid (204 mg, 1.50 mmol) using 1/2 mol % of Pd(OAc)2/Ph5FcP(t-Bu)2 and KF (180 mg, 3.10 mmol) in THF at 50° C. to give the title compound (189 mg, 96%) as a white solid: 1H-NMR (400 MHz, CDCl3): δ 9.98 (s, 1H), 7.85 (d, 2H, J=8.2 Hz), 7.41 (d, 2H, J=8.1 Hz), 7.22-7.13 (m, 4H), 2.19 (s, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 191.98, 148.36, 140.51, 135.06, 134.87, 130.54, 129.88, 129.55, 129.42, 128.03, 125.94, 20.34. GC/MS(EI): m/z 196 (M+), 165, 167, 152. Anal. Calcd for C14H12O: C, 85.68; H, 6.16. Found: C, 85.64; H, 6.39. at 50° C.

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

Procedure: 4-Chlorobenzaldehyde (144 mg, 1.02 mmol) reacted with 2-methylphenylboronic acid (204 mg, 1.50 mmol) using 1/2 mol % of Pd(OAc)2/Ph5FcP(t-Bu)2 and KF (180 mg, 3.10 mmol) in THF at 50° C. to give the title compound (189 mg, 96%) as a white solid: 1H-NMR (400 MHz, CDCl3): δ 9.98 (s, 1H), 7.85 (d, 2H, J=8.2 Hz), 7.41 (d, 2H, J=8.1 Hz), 7.22-7.13 (m, 4H), 2.19 (s, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 191.98, 148.36, 140.51, 135.06, 134.87, 130.54, 129.88, 129.55, 129.42, 128.03, 125.94, 20.34. GC/MS(EI): m/z 196 (M+), 165, 167, 152. Anal. Calcd for C14H12O: C, 85.68; H, 6.16. Found: C, 85.64; H, 6.39. at 50° C.

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

Procedure: 2′-Methyl[1,1′-biphenyl]-4-carbaldehyde and (1S)-1,2,3,4-tetrahydro-1-naphthalenylamine were processed as described in Example 1A to provide the title compound.

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

Procedure: The method described in Referential Example 237 was performed by use of 2-bromotoluene and 4-formylbenzene boronic acid, whereby the title compound was obtained.

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

Procedure: A suspension of N,N-dimethyl-1H-imidazole-1-sulfonamide (2.02 g) in THF (50 mL) was cooled to −78° C., and thereto was added dropwise n-BuLi (4.77 mL, 2.66 M hexane solution), and the mixture was stirred for 30 minutes. To the mixture was added p-tolyl benzaldehyde (2.08 g), and the mixture was warmed to room temperature over a period of 1 hour, and then stirred for 16 hours. The mixture was extracted with aqueous hydrochloric acid solution, washed with Et2O, and basified with an aqueous NaOH solution. This solution was extracted with Et2O, and the organic layer was dried and filtered. The solvent was evaporated under reduced pressure to give 2-[hydroxy(4-methylphenyl)methyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide. the mixture was warmed to room temperature over a period of 1 hour stirred for 16 hours The mixture was extracted with aqueous hydrochloric acid solution washed with Et2O This solution was extracted with Et2O the organic layer was dried filtered The solvent was evaporated under reduced pressure

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

Procedure: 4-Chlorobenzaldehyde (144 mg, 1.02 mmol) reacted with 2-methylphenylboronic acid (204 mg, 1.50 mmol) using 1/2 mol % of Pd(OAc)2/Ph5FcP(t-Bu)2 and KF (180 mg, 3.10 mmol) in THF at 50° C. to give the title compound (189 mg, 96%) as a white solid: 1H-NMR (400 MHz, CDCl3): δ 9.98 (s, 1H), 7.85 (d, 2H, J=8.2 Hz), 7.41 (d, 2H, J=8.1 Hz), 7.22-7.13 (m, 4H), 2.19 (s, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 191.98, 148.36, 140.51, 135.06, 134.87, 130.54, 129.88, 129.55, 129.42, 128.03, 125.94, 20.34. GC/MS(EI): m/z 196 (M+), 165, 167, 152. Anal. Calcd for C14H12O: C, 85.68; H, 6.16. Found: C, 85.64; H, 6.39. at 50° C.