5-(3,4-Diethoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazole → HCID 66726622, compound

HRID 710437Notes

Reaction equation

HRID 710437 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[NH:22][CH:21]=[CH:20]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH3:11].C(OC1C=C(C2ON=C(C3C=CC=C4C=3C=CN4)N=2)C=CC=1OCC)C>>[Br:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[NH:22][CH2:21][CH2:20]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH3:11]

Participants

3

Reactant 2

HCID 251102975-(3,4-Diethoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazoleHCID 66726256HCID 66726256, compound

Product 1

HCID 66726622HCID 66726622, compoundYield 95%

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 in 95% yield. 1H-NMR (CDCl3) 1.10 (tr, 3H, J=7.38 Hz); 1.85-1.94 (m, 2H); 3.54 (tr, 2H, J=7.92 Hz); 3.75 (tr, 2H, J=8.28 Hz); 4.08 (tr, 2H, J=6.42 Hz); 6.98 (d, 1H, J=8.73 Hz); 7.03 (d, 1H, J=7.77 Hz); 7.26 (tr, 1H, J=7.83 Hz); 7.75 (d, 1H, J=7.17 Hz); 8.09 (dd, 1H, J=2.1, 8.61 Hz); 8.39 (d, 1H, J=2.1 Hz).

Sources & evidence

ORD record
ord-5f60cedaac6149708fa68436c92e43a5
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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