3-Chloro-4-propoxybenzoic acid → 5-(3-chloro-4-propoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazole

HRID 710417Notes

Reaction equation

HRID 710417 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][CH3:14])[C:5]([OH:7])=O.C(OC1C=C(C2O[N:32]=[C:31]([C:34]3[CH:42]=[CH:41][CH:40]=[C:39]4[C:35]=3[CH:36]=[CH:37][NH:38]4)[N:30]=2)C=CC=1OCCC)CC>>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:7][N:32]=[C:31]([C:34]3[CH:42]=[CH:41][CH:40]=[C:39]4[C:35]=3[CH:36]=[CH:37][NH:38]4)[N:30]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 87071503-Chloro-4-propoxybenzoic acidHCID 667262635-(3,4-dipropoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazole

Product 1

HCID 667262915-(3-chloro-4-propoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazoleYield 35%

Procedure

When the product of Step C was substituted for 5-(3,4-dipropoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazole in Example 43 Step C, the similar process afforded the title compound in 35% yield, as off white solid. 1H-NMR (CDCl3) 1.1 (tr, 3H, J=7.37 Hz); 1.78-1.95 (m, 2H); 4.09 (t, 2H, J=6.47 Hz); 7.03 (d, 1H, J=8.66 Hz); 7.34-7.39 (m, 3H); 7.56 (d, 1H, J=8.14 Hz); 8.04 (d, 1H, J=6.8 Hz); 8.1 (dd, 1H, J=8.6, 2.1 Hz); 8.28 (d, 1H, J=3.21 Hz); 8.38 (broad s, 1H).

Sources & evidence

ORD record
ord-cf21febd3d3744f7bc799d911d56cb96
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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