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

HRID 710430Notes

Reaction equation

HRID 710430 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[NH:24][CH:23]=[CH:22]4)[N:15]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].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:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[NH:24][CH2:23][CH2:22]4)[N:15]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

3

Reactant 2

HCID 251102975-(3,4-Diethoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazoleHCID 667268455-(3-Chloro-4-(pentyloxy)phenyl)-3-(1H-indol-5-yl)-1,2,4-oxadiazole

Product 1

HCID 667267755-(3-Chloro-4-(pentyloxy)phenyl)-3-(indolin-5-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 in 100% yield. 1H-NMR (CDCl3) 0.94 (tr, 3H, J=7.11 Hz); 1.44-1.54 (m, 4H); 1.66-2.03 (m, 2H); 3.45 (tr, 2H, J=8.16 Hz); 3.65 (tr, 2H, J=7.83 Hz); 4.11 (tr, 2H, J=6.51 Hz); 6.75 (d, 1H, J=7.68 Hz); 7.00 (d, 1H, J=8.67 Hz); 7.20 (tr, 1H, J=6.24 Hz); 7.51 (broad d, 1H, J=7.77 Hz); 8.04 (dd, 1H, J=2.13, 8.64 Hz); 8.21 (d, 1H, J=2.1 Hz).

Sources & evidence

ORD record
ord-e686c523b1dc43fcab12c1ba7abd20b9
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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