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

HRID 710396Notes

Reaction equation

HRID 710396 reaction equation
[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]5[O:22][C:21]([CH3:23])=[CH:20][C:19]=5[CH:24]=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]5[O:22][C:21]([CH3:23])=[CH:20][C:19]=5[CH:24]=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 667266073-(1H-Indol-4-yl)-5-(2-methylbenzofuran-5-yl)-1,2,4-oxadiazole

Product 1

HCID 667266113-(Indolin-4-yl)-5-(2-methylbenzofuran-5-yl)-1,2,4-oxadiazoleYield 100%

Procedure

When the product of Step D was 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 100% yield, as a colourless foam. 1H-NMR (CDCl3) 2.49 (s, 3H); 2.52 (broad s, 1H+H2O); 3.48 (tr, 2H, J=8.44 Hz); 3.68 (tr, 2H, J=8.44 Hz); 6.48 (s, 1H); 6.85 (d, 1H, J=7.75 Hz); 7.2 (tr, 2H, J=7.6 Hz); 7.38 (d, 1H, J=8.16 Hz); 7.51 (d, 1H, J=8.5 Hz); 8.06 (d, 1H, J=8.5 Hz); 8.32 (s, 1H).

Sources & evidence

ORD record
ord-2c7bc2834b614b67991b3a9e9f03907c
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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