4-bromo-2-chloro-1-(trifluoromethyl)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 as described for 3,4-bis(benzyloxy)-6-((3-methyl-4-(trifluoromethyl)-phenyl)ethynyl)pyridazine (Intermediate 74) using 4-bromo-2-chloro-1-(trifluoro-methyl)benzene in 98% yield. Prepared

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

Procedure: Prepared as described for 3,4-bis(benzyloxy)-6-((3-methyl-4-(trifluoromethyl)-phenyl)ethynyl)pyridazine (Intermediate 74) using 4-bromo-2-chloro-1-(trifluoro-methyl)benzene in 98% yield. Prepared

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

Procedure: The title compound was prepared in analogy to example 148 step F) from 8-(2-chloro-benzenesulfonyl)-2,8-diaza-spiro[4.5]decan-1-one (described in example 148 step E or example 179 step A for an alternative synthesis) and 4-bromo-2-chloro-1-trifluoromethyl-benzene. Off-white solid. MS (ESI): 507.1 (MH+).

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

Procedure: In analogy to the procedure described for intermediate 31, 4-bromo-2-chloro-1-trifluoromethyl-benzene and tert-butyl 3-bromopropionate gave the title compound in 53% yield as yellow oil. MS: 323 (M+, Cl).

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: DABCO (86.4 mg, 0.7 mmol), Pd(OAc)2 (86.5 mg, 0.38 mmol), 4-bromo-2-chloro-1-(trifluoromethyl)benzene (5.0 g, 19.2 mmol) and ethyl acrylate (2.86 g, 28.9 mmol) were added to a stirred solution of K2CO3 (2.6 g, 19.27 mmol) in DMF degassed previously for 20 minutes. The resulting mixture was stirred for 1 hour at 110° C. The reaction was monitored by TLC (5% ethyl acetate in hexane). Purification by column chromatography on silica gel (5% ethyl acetate in hexane) afforded 5.0 g of the product (94.3% yield). degassed previously for 20 minutes Purification by column chromatography on silica gel (5% ethyl acetate in hexane)

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

Procedure: Prepared as described for 3,4-bis(benzyloxy)-6-((3-methyl-4-(trifluoromethyl)-phenyl)ethynyl)pyridazine (Intermediate 74) using 4-bromo-2-chloro-1-(trifluoro-methyl)benzene in 98% yield. Prepared