. Author manuscript; available in PMC: 2014 Jul 22.

Published in final edited form as: Tetrahedron. 2013 Jul 22;69(29):5829–5840. doi: 10.1016/j.tet.2013.05.045

Table 3.

Synthesis of 1,5-Disubstituted-5-Indole Appended Pyrazoles from Vinylogous Amide

Entry	Cpd.	R	% Yield (purified)	Solvent	Heat Source
1	17a	4-Methylphenyl	82	CH₃CN	Microwave, 85°C for 2 hrs
2	17b	4-Chlorophenyl	93	CH₃CN	Microwave, 85°C for 2 hrs
3	17c	4-Bromophenyl	97	CH₃CN	Microwave, 85°C for 2 hrs
4	17d	Phenyl	52	CH₃CN	Microwave, 85°C for 2 hrs
5	17e	4-Methoxyphenyl	84	CH₃CN	Microwave, 85°C for 2hrs
6	17c	4-Bromophenyl	82	HOAC	Microwave, 85°C for 2hrs
7	17c	4-Bromophenyl	70	EtOH	Microwave, 85°C for 2hrs
8	17c	4-Bromophenyl	69	CH₃CN	Reflux for 4 hr
9	17a	4-Methylphenyl	60	HOAc	Reflux for 4 hr
10	17b	4-Chlorophenyl	56	HOAc	Reflux for 4 hr
11	17c	4-Bromophenyl	82	HOAc	Reflux for 4 hr
12	17d	Phenyl	51	HOAc	Reflux for 4 hr
13	17e	4-Methoxyphenyl	51	HOAc	Reflux for 4 hr
14	17f	H	75	HOAc	Reflux for 18 hr
15	17g	Me	59 (10:1 mix of the 1,5- to the 1,3-isomer by GC-MS)	HOAc	Reflux for 18 hr
16	17h	Et	69 (6:1 mix of the 1,5- to the 1,3-isomer by GC-MS)	HOAc	Reflux for 18 hr
17	17i	t-Bu	80 (32:1 mix of the 1,5- to the 1,3-isomer by GC-MS)	EtOH	Reflux for 18 hr
18	17h	Et	96 (78:1 mix of the 1,5- to the 1,3-isomer by GC-MS)	CH₃CN	Reflux for 18 hr
19	17i	t-Bu	85 (22:1 mix of the 1,5- to the 1,3-isomer by GC-MS)	CH₃CN	Reflux for 18 hr