5-Methoxyindole → 5-methoxy-2,3-dihydro-1H-indole

HRID 710300Notes

Reaction equation

HRID 710300 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.ClC1C=C(C2ON=C(C3C=C4C(=CC=3)NC=C4)N=2)C=CC=1OC>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6]2

Participants

3

Reactant 2

HCID 138725-MethoxyindoleHCID 667266895-(3-chloro-4-methoxyphenyl)-3-(1H-indol-5-yl)-1,2,4-oxadiazole

Product 1

HCID 107019745-methoxy-2,3-dihydro-1H-indoleYield 84%

Procedure

When 5-methoxy-1H-indole was substituted for 5-(3-chloro-4-methoxyphenyl)-3-(1H-indol-5-yl)-1,2,4-oxadiazole in Example 7, Step F, the identical process afforded the title compound in 84% yield., as a creamy syrup. 1H-NMR (CDCl3) 2.99 (tr, 2H, J=8.35 Hz); 3.28 (broad s, 1H); 3.52 (tr, 2H, J=8.35 Hz); 3.73 (s, 3H); 6.57 (m, 2H); 6.75 (s, 1H).

Sources & evidence

ORD record
ord-38904ffdcc9c45119896859e54852a6e
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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