3-Nitrobenzylamine → 5-Aminoindole

HRID 1615607Notes

Reaction equation

HRID 1615607 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:3]=1[C:4]#N.[N+:13]([C:16]1C=C(C=CC=1)CN)([O-])=O>C(O)C>[NH2:10][C:7]1[CH:6]=[C:3]2[C:2](=[CH:9][CH:8]=1)[NH:13][CH:16]=[CH:4]2

Participants

4

Reactant 2

HCID 1227223-NitrobenzylamineHCID 5194172-Fluoro-5-nitrobenzonitrile

Product 1

HCID 788675-Aminoindole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 84 was prepared using methods shown in Example 1, wherein 2-fluoro-5-nitrobenzonitrile was reacted with 3-nitrobenzyl amine in Step A. Following steps B through E, the 3-nitrobenzyl intermediate was reduced using stannous chloride in ethanol to provide the corresponding 5-amino indole intermediate. Dimethylation of the 5-amino group was carried out using aqueous formaldehyde solution (37% w/w, 10 eq.) and MP-cyanoborohydride resion (2.42 mmol/g, 1.5 eq.) in methanol:acetic acid (9:1, v/v) at room temperature for about 15 hours.

Sources & evidence

ORD record
ord-9e79d1beb88944ec96ed55ed32e59645
Source dataset
uspto-grants-2014_07
Patent number
US08765757B2

Reaction notes

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