1-bromoheptan-2-one

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: By the same method, 1-bromo-2-heptanone, 3-bromo-4-heptanone and 4-bromo-2,5-dimethyl-3-hexanone are converted to 2-amino-4-pentylthiazole, 2-amino-4-ethyl-5-propylthiazole and 2-amino-4,5-diisopropylthiazole, respectively.

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

Procedure: By the same method, 1-bromo-2-heptanone, 3-bromo-4-heptanone and 4-bromo-2,5-dimethyl-3-hexanone are converted to 2-amino-4-pentylthiazole, 2-amino-4-ethyl-5-propylthiazole and 2-amino-4,5-diisopropylthiazole, respectively.

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

Procedure: By the same method, 1-bromo-2-heptanone, 3-bromo-4-heptanone and 4-bromo-2,5-dimethyl-3-hexanone are converted to 2-amino-4-pentylthiazole, 2-amino-4-ethyl-5-propylthiazole and 2-amino-4,5-diisopropylthiazole, respectively.

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

Procedure: By the same method, 1-bromo-2-heptanone, 3-bromo-4-heptanone and 4-bromo-2,5-dimethyl-3-hexanone are converted to 2-amino-4-pentylthiazole, 2-amino-4-ethyl-5-propylthiazole and 2-amino-4,5-diisopropylthiazole, respectively.

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

Procedure: Following the procedure as described in Example 2, making variations only as required to 1-bromoheptan-2-one in place of 1-bromobutan-2-one to react with [4-(6-aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)methanone, the title compound was obtained as a white solid in 62% yield. 1H NMR (300 MHz, CDCl3) δ 7.71-7.69 (m, 1H), 7.64-7.49 (m, 3H), 7.42 (s, 1H), 7.34-7.32 (m, 1H), 6.7 (d, J=9.9 Hz, 1H), 4.01-3.83 (m, 2H), 3.57-3.48 (m, 2H), 3.37-3.27 (m, 4H), 2.73-2.68 (m, 2H), 1.75-1.65 (m, 2H), 1.4-1.25 (m, 4H), 0.91 (t, J=6.9 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ 167.5, 154.3, 146.8, 135.7, 134.4, 132.3, 129.4, 127.1, 126.8, 126.7, 126.6, 125.4, 125.3, 121.8, 113.6, 109.3, 46.5, 46.4, 46.2, 41.1, 31.5, 29.1, 29.07, 22.5, 14.0. MS (ES+) m/z 446.2 (M+1).

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

Procedure: To a stirred solution of 3-methoxythiophenolate (45 g) in water (100 mL) at 15° C. was added dropwise over 20 minutes 1-bromo-2-heptanone (54.4 g). The reaction was stirred for 1 hour at room temperature then was extracted with diethyl ether (2×250 mL) and the ether extracts were washed in turn with water (2×100 mL) and 1N hydrochloric acid (2×100 mL). The dried (MgSO4) organic layers were combined and evaporated to yield crude 1-(3-methoxyphenylthio)-2-heptanone (71 g). The crude 1-(3-methoxyphenylthio)-2-heptanone (65 g) was added over 30 minutes with stirring to sulfuric acid at -10° C. After 30 minutes at -5° C., the reaction mixture was diluted carefully with ice (200 g) and the resulting solid was filtered off, washed with water and dried. Crystallization of the crude product from hexane gave 18.4 g of 6-methoxy-3-pentylbenzo[b]thiophene, mp 43°-45° C. A small sample was recrystallized from hexane to provide the analytical specimen, mp 45°-47° C. Anal. Calcd for C14H18OS: C, 71.75; H, 7.74; S, 13.68 Found: C, 71.81; H, 7.60; S, 13.37 then was extracted with diethyl ether (2×250 mL) the ether extracts were washed in turn with water (2×100 mL) and 1N hydrochloric acid (2×100 mL) The dried (MgSO4) organic layers evaporated

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

Procedure: By the same method, 1-bromo-2-heptanone, 3-bromo-4-heptanone and 4-bromo-2,5-dimethyl-3-hexanone are converted to 2-amino-4-pentylthiazole, 2-amino-4-ethyl-5-propylthiazole and 2-amino-4,5-diisopropylthiazole, respectively.

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

Procedure: By the same method, 1-bromo-2-heptanone, 3-bromo-4-heptanone and 4-bromo-2,5-dimethyl-3-hexanone are converted to 2-amino-4-pentylthiazole, 2-amino-4-ethyl-5-propylthiazole and 2-amino-4,5-diisopropylthiazole, respectively.

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

Procedure: By the same method, 1-bromo-2-heptanone, 3-bromo-4-heptanone and 4-bromo-2,5-dimethyl-3-hexanone are converted to 2-amino-4-pentylthiazole, 2-amino-4-ethyl-5-propylthiazole and 2-amino-4,5-diisopropylthiazole, respectively.