5-(3,4-dipropoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazole → 5-(3-Chloro-4-ethoxyphenyl)-3-(indolin-4-yl)-1,2,4-oxadiazole

HRID 710413Notes

Reaction equation

HRID 710413 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:17]=3[CH:18]=[CH:19][NH:20]4)[N:12]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH3:10].C(OC1C=C(C2ON=C(C3C=CC=C4C=3C=CN4)N=2)C=CC=1OCCC)CC>>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:17]=3[CH2:18][CH2:19][NH:20]4)[N:12]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH3:10]

Participants

3

Reactant 2

HCID 667262635-(3,4-dipropoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazoleHCID 667268385-(3-chloro-4-ethoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazole

Product 1

HCID 667268775-(3-Chloro-4-ethoxyphenyl)-3-(indolin-4-yl)-1,2,4-oxadiazoleYield 100%

Procedure

When the product of Step B was substituted for 5-(3,4-dipropoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazole in Example 43 Step D, the similar process afforded the title compound in 100% yield, as a creamy solid. 1H-NMR (CDCl3) 1.52 (tr, 3H, J=6.95 Hz); 3.69 (tr, 2H, J=7.53 Hz); 3.92 (tr, 2H, J=7.43 Hz); 4.18 (q, 2H, J=6.98 Hz); 7.03 (d, 1H, J=8.67 Hz); 7.39-7.45 (m, 2H), 7.94-8.10 (m, 2H), 8.21 (d, 1H, J=2.07 Hz).

Sources & evidence

ORD record
ord-627532f4a9c74b4b828cbadcf012e696
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

Loading…