Methylamine → 5-Aminoindole

HRID 1615606Notes

Reaction equation

HRID 1615606 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:3]=1[C:4]#N.CN.C(OC)(=O)C1[C:17](=CC=CC=1)[NH2:18]>C(O)C>[NH2:10][C:7]1[CH:6]=[C:3]2[C:2](=[CH:9][CH:8]=1)[NH:18][CH:17]=[CH:4]2

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8635Methyl AnthranilateHCID 5194172-Fluoro-5-nitrobenzonitrile

Product 1

HCID 788675-Aminoindole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 245 was prepared using methods shown in Example 1, wherein 2-fluoro-5-nitrobenzonitrile and methylamine were used in Step A and methyl anthranilate was used in Step D. Reduction of the 5-nitro group was carried out 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-63d4d73a52bd4a4c9355fff4d3aea889
Source dataset
uspto-grants-2014_07
Patent number
US08765757B2

Reaction notes

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