Lithium amide → 5-Methoxy-1-methyl-3-[(1-methylethyl)thio]-1H-indole-2-carboxamide

HRID 21596

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7]([C:13](OC)=[O:14])=[C:6]2[S:17][CH:18]([CH3:20])[CH3:19].[NH2-:21].[Li+]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7]([C:13]([NH2:21])=[O:14])=[C:6]2[S:17][CH:18]([CH3:20])[CH3:19]

Participants

Reactant 2

HCID 24532Lithium amide

HCID 15294536methyl 5-methoxy-1-methyl-3-[(1-methylethyl)thio]-1H-indole-2-carboxylate

Product 1

HCID 152945335-Methoxy-1-methyl-3-[(1-methylethyl)thio]-1H-indole-2-carboxamideYield 68%

Procedure

Prepared from methyl 5-methoxy-1-methyl-3-[(1-methylethyl)thio]-1H-indole-2-carboxylate and lithium amide as described in Example 23. Yield 68% after recrystallization from ethyl acetate-hexane; mp 122°-124° C.

Workup

customYield 68% after recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record: ord-a7f979b7f8b24b2c95f16e4a87726e4b
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05424329

Linked notes

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