1-(2-bromoethyl)piperidine

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: In an analogous manner to that described in Example 1, from diethyl 2-amino-6-[(hydroxycarbamoyl)-methyl]-azulene-1,3-dicarboxylate sodium and 2-piperidinoethyl bromide the title compound of m.p. 163-165° C. is obtained in 7% yield.

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

Procedure: Was prepared in an analogous manner to 1-propylindoline-2,3-dione using commercially available 5-chloroisatin (purchased from Fisher Scientific) and 1-(2-bromoethyl)piperidine (purchased from Fisher Scientific). 1H-NMR δ 7.55 (m, 2H), 6.95 (d, 1H), 3.84 (t, 2H), 2.58 (t, 2H), 2.46 (bs, 4H), 1.54 (m, 4H), 1.43 (m, 2H).

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

Procedure: The title compound was prepared in a manner similar to that described in Example 2 from methyl 2-(tert-butoxy)-2-(4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate and 1-(2-bromoethyl)piperidine. 1H NMR (400 MHz, METHANOL-d4) ppm 7.62-7.52 (m, 3H), 7.48-7.41 (m, 1H), 7.39-7.31 (m, 1H), 6.09-6.03 (m, 1H), 5.27 (s, 1H), 5.00-4.91 (m, 2H), 3.75 (s, 3H), 3.68-3.53 (m, 4H), 3.12-2.95 (m, 2H), 2.04-1.92 (m, 2H), 1.92-1.75 (m, 2H), 1.62-1.46 (m, 2H), 0.96 (s, 9H); LCMS (m/z) ES+=500 (M+1).