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

HRID 710425Notes

Reaction equation

HRID 710425 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([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:8][C:7]=1[Cl:26])[CH2:2][CH2:3][CH3:4].C(OC1C=C(C2ON=C(C3C=CC=C4C=3C=CN4)N=2)C=CC=1OCC)C>>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([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:8][C:7]=1[Cl:26])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 251102975-(3,4-Diethoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazoleHCID 667265825-(4-butoxy-3-chlorophenyl)-3-(1H-indol-5-yl)-1,2,4-oxadiazole

Product 1

HCID 667268185-(4-Butoxy-3-chlorophenyl)-3-(indolin-5-yl)-1,2,4-oxadiazoleYield 92%

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 92% yield. 1H-NMR CDCl3) 0.97 (tr, 3H, J=8.34 Hz), 1.41-1.6 (m, 2H); 1.76-1.91 (m, 2H); 3.45 (tr, 2H, J=8.16 Hz; 3.63 (tr, 2H); 4.10 (tr, 2H, J=6.45 Hz); 6.75 (d, 1H, J=7.56 Hz); 7.06 (d, 1H, J=7.11 Hz); 7.18 (tr, 1H, J=7.77 Hz); 7.51 (broad d, 1H, J=7.8 Hz); 8.04 (dd, 1H, J=2.07-8.61 Hz); 8.21 (d, 1H, J=2.07 Hz).

Sources & evidence

ORD record
ord-f1738eff32ce4e948b55cd1dfa9959e5
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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