5-(3,4-Diethoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazole → 3-(Indolin-4-yl)-5-(2'-(trifluoromethyl)biphenyl-4-yl)-1,2,4-oxadiazole

HRID 710377Notes

Reaction equation

HRID 710377 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[N:14]=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=5[C:27]([F:30])([F:29])[F:28])=[CH:17][CH:16]=4)[O:12][N:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(OC1C=C(C2ON=C(C3C=CC=C4C=3C=CN4)N=2)C=CC=1OCC)C>>[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[N:14]=[C:13]([C:15]4[CH:16]=[CH:17][C:18]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=5[C:27]([F:30])([F:28])[F:29])=[CH:19][CH:20]=4)[O:12][N:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 251102975-(3,4-Diethoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazoleHCID 667267123-(1H-Indol-4-yl)-5-(2'-(trifluoromethyl)biphenyl-4-yl)-1,2,4-oxadiazole

Product 1

HCID 667267333-(Indolin-4-yl)-5-(2'-(trifluoromethyl)biphenyl-4-yl)-1,2,4-oxadiazoleYield 99%

Procedure

When the product of Step C is substituted for 5-(3,4-diethoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazole in Example 34, Step C, the identical process afforded the title compound in 99% yield., as a colourless foam. 1H-NMR (CDCl3) 3.49 (tr, 2H, J=8.7 Hz); 3.66 (tr, 2H, J=8.7 Hz); 4.09 (broad s, 1H); 6.76 (d, 1H, J=7.6 Hz); 7.16 (tr, 1H, J=7.2 Hz); 7.34 (d, 1H, J=7.6 Hz); 7.4-7.63 (m, 5H); 7.77 (d, 1H, J=7.6 Hz); 8.24 (d, 1H, J=8.5 Hz).

Sources & evidence

ORD record
ord-dbb9f03fdb4a48b49d741340b9c3c3a7
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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