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

HRID 710418Notes

Reaction equation

HRID 710418 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH:19]=[CH:20][NH:21]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>>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH2:19][CH2:20][NH:21]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 667262915-(3-chloro-4-propoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazole

Product 1

HCID 667265905-(3-Chloro-4-propoxyphenyl)-3-(indolin-4-yl)-1,2,4-oxadiazoleYield 99%

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 99% yield. 1H-NMR (CDCl3) 1.09 (tr, 3H, J=7.37 Hz); 1.81-1.94 (m, 2H); 3.51 (tr, 2H, J=8.08 Hz); 3.71 (tr, 2H, J=8.48 Hz); 4.08 (tr, 2H, J=6.47 Hz); 6.92 (d, 1H, J=7.44 Hz); 7.00 (d, 1H, J=8.72 Hz); 7.22 (tr, 1H, J=7.85 Hz); 7.65 (d, 1H, J=7.78 Hz); 8.04 (dd, 1H, J=8.63, 2.11 Hz); 8.21 (d, 1H, J=2.09 Hz).

Sources & evidence

ORD record
ord-58b33b27e5e547469bcd8c0605270e4a
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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