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

HRID 21595

Reaction equation

HRID 21595 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:8][CH:9]=2)[C:4]([S:19][CH:20]([CH3:22])[CH3:21])=[C:3]1[C:23]([O:25]CC)=O.[NH2-:28].[Li+]>>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:8][CH:9]=2)[C:4]([S:19][CH:20]([CH3:22])[CH3:21])=[C:3]1[C:23]([NH2:28])=[O:25]

Participants

3

Reactant 2

HCID 24532Lithium amideHCID 15294535ethyl 1-methyl-3-[(1-methylethyl)thio]-5-(phenylmethoxy)-1H-indole-2-carboxylate

Product 1

HCID 152945321-Methyl-3-[(1-methylethyl)thio]-5-(phenylmethoxy)-1H-indole-2-carboxamideYield 78%

Procedure

Prepared from ethyl 1-methyl-3-[(1-methylethyl)thio]-5-(phenylmethoxy)-1H-indole-2-carboxylate and lithium amide as described in Example 18. After evaporation of excess ammonia, the residue is treated with ice water. The insoluble material is filtered and washed with water, then recrystallized from ethyl acetate-hexane. Yield 78%; mp 151°-154° C.

Workup

  1. customAfter evaporation of excess ammonia
  2. additionthe residue is treated with ice water
  3. filtrationThe insoluble material is filtered
  4. washwashed with water
  5. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a14145a8404a40248665186c7668a3e0
Source dataset
uspto-grants-1995_06
Patent number
US05424329

Linked notes

Loading…