4-bromo-2-methoxyphenol

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:

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:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (S)-tert-butyl 2-(((methylsulfonyl)oxy)methyl)pyrrolidine-1-carboxylate (279 mg, 1.00 mmol) and 4-bromo-2-methoxyphenol (325 mg, 1.57 mmol) in N,N-dimethylformamide (5.55 mL) was added cesium carbonate (651 mg, 2.00 mmol). The mixture was heated to 100° C. After 22 h, the mixture was allowed to cool to 23° C. and diluted with water (30 mL). The mixture was extracted with ethyl acetate (3×30 mL). The combined organics were dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo. Purification by column chromatography (silica gel, 0-50% ethyl acetate in dichloromethane) afforded the title compound as an amber oil. MS (ES+) 408.2 (M+Na)+. 1H NMR (400 MHz, CDCl3): δ 7.07-6.79 (m, 3H), 4.25-4.10 (m, 2H), 4.01-3.73 (m, 1H), 3.84 (s, 3H), 3.48-3.26 (m, 2H), 2.16-1.80 (m, 4H), 1.48 (s, 9H). to cool to 23° C. The mixture was extracted with ethyl acetate (3×30 mL) The combined organics were dried over sodium sulfate filtered The filtrate was concentrated in vacuo Purification by column chromatography (silica gel, 0-50% ethyl acetate in dichloromethane)

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

Procedure: The title compound was prepared by substituting Example 652A for 2-(4-methylthiazol-5-yl)-ethanol and 2-methoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol for 4-bromo-2-methoxyphenol, respectively, in Example 630A. MS (ESI) m/e 426 (M+H)+; 1H NMR (300 MHz, DMSO-d.6 □ 7.77 (s, 1H), 7.25 (dd, J=8.1, 1.4 Hz, 1H), 7.15 (d, J=1.4 Hz, 1H), 7.09 (d, J=8.1 Hz, 1H), 5.15 (s, 2H), 3.77 (s, 3H), 1.28 (s, 12H).

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

Procedure: The title compound was prepared by substituting Example 652A for 2-(4-methylthiazol-5-yl)-ethanol and 2-methoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol for 4-bromo-2-methoxyphenol, respectively, in Example 630A. MS (ESI) m/e 426 (M+H)+; 1H NMR (300 MHz, DMSO-d.6 □ 7.77 (s, 1H), 7.25 (dd, J=8.1, 1.4 Hz, 1H), 7.15 (d, J=1.4 Hz, 1H), 7.09 (d, J=8.1 Hz, 1H), 5.15 (s, 2H), 3.77 (s, 3H), 1.28 (s, 12H).

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

Procedure: The title compound was prepared by substituting 2-chloromethyl-1-methyl-1H-imidazole hydrochloride and 4-bromo-2-methoxyphenol for Example 627A and Example 474, respectively, in Example 627B. MS (ESI) m/e 329 (M+H)+; 1H NMR (300 MHz, DMSO-d6) □ 7.17 (d, J=1.2 Hz, 1H), 7.11-7.15 (m, 2H), 7.05 (dd, J=8.5, 2.0 Hz, 1H), 6.85 (d. J=1.0 Hz, 1H), 5.09 (s, 2H), 3.77 (s, 3H), 3.67 (s, 3H).

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

Procedure: The title compound was prepared by substituting 2-chloromethyl-1-methyl-1H-imidazole hydrochloride and 4-bromo-2-methoxyphenol for Example 627A and Example 474, respectively, in Example 627B. MS (ESI) m/e 329 (M+H)+; 1H NMR (300 MHz, DMSO-d6) □ 7.17 (d, J=1.2 Hz, 1H), 7.11-7.15 (m, 2H), 7.05 (dd, J=8.5, 2.0 Hz, 1H), 6.85 (d. J=1.0 Hz, 1H), 5.09 (s, 2H), 3.77 (s, 3H), 3.67 (s, 3H).