3,4-Diethoxybenzoic acid → 3-(4-Bromophenyl)-5-(3,4-diethoxyphenyl)-1,2,4-oxadiazole

HRID 710441Notes

Reaction equation

HRID 710441 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[NH:9])[NH:7][OH:8])=[CH:4][CH:3]=1.ONC(C1C2C=CNC=2C=CC=1)=N.[CH2:25]([O:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=1[O:37][CH2:38][CH3:39])[C:31](O)=O)[CH3:26].C(OC1C=C(C=CC=1OCCC)C(O)=O)CC>>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[N:9]=[C:31]([C:30]3[CH:34]=[CH:35][C:36]([O:37][CH2:38][CH3:39])=[C:28]([O:27][CH2:25][CH3:26])[CH:29]=3)[O:8][N:7]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 794173,4-Diethoxybenzoic acidHCID 24429763,4-Dipropoxybenzoic acidHCID 178513245HCID 178513245, compoundHCID 178513279HCID 178513279, compound

Product 1

HCID 21992353-(4-Bromophenyl)-5-(3,4-diethoxyphenyl)-1,2,4-oxadiazoleYield 58%

Procedure

When the product of Step A was substituted for N-hydroxy-1H-indole-4-carboximidamide and 3,4-diethoxybenzoic acid was substituted for 3,4-dipropoxybenzoic acid in Example 43, Step C the similar process afforded the title compound in 58% yield. 1H-NMR (CDCl3) 1.47-1.53 (m, 6H); 4.14-4.24 (m, 4H); 6.97 (d, 1H, J=8.48 Hz); 7.61-7.66 (m, 3H); 7.77 (dd, 1H, J=1.98, 8.42 Hz); 8.00 (d, 2H, J=8.55 Hz).

Sources & evidence

ORD record
ord-171fbc14f435432889cd3477abc8b5bb
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

Loading…