5-(3,4-Diethoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazole → 5-(4-Ethoxy-3-methoxyphenyl)-3-(indolin-4-yl)-1,2,4-oxadiazole

HRID 710434Notes

Reaction equation

HRID 710434 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:23]=[CH:22][CH:21]=[C:20]4[C:16]=3[CH:17]=[CH:18][NH:19]4)[N:11]=2)=[CH:6][C:5]=1[O:24][CH3:25])[CH3:2].C(OC1C=C(C2ON=C(C3C=CC=C4C=3C=CN4)N=2)C=CC=1OCC)C>>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:23]=[CH:22][CH:21]=[C:20]4[C:16]=3[CH2:17][CH2:18][NH:19]4)[N:11]=2)=[CH:6][C:5]=1[O:24][CH3:25])[CH3:2]

Participants

3

Reactant 2

HCID 251102975-(3,4-Diethoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazoleHCID 667265925-(4-ethoxy-3-methoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazole

Product 1

HCID 667269465-(4-Ethoxy-3-methoxyphenyl)-3-(indolin-4-yl)-1,2,4-oxadiazoleYield 100%

Procedure

When the product of Step C 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 100% yield. 1H-NMR (CDCl3) 1.5 (tr, 3H, J=3.98 Hz); 3.6 (tr, 2H, J=7.79 Hz); 3.8 (tr, 2H, J=8.87 Hz); 3.99 (s, 3H); 4.19 (q, 2H, J=14, 7 Hz); 6.97 (d, 1H, J=8.5 Hz); 7.17 (d, 1H, J=7.79 Hz); 7.32 (tr, 1H, J=7.82 Hz); 7.66 (d, 1H, J=1.92 Hz); 7.67 (dd, 1H, J=1.97, 8.41 Hz), 7.89 (d, 1H, J=7.78 Hz).

Sources & evidence

ORD record
ord-4bedb07871fd46b9bb28a5ff61f59d7a
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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