HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Dimethylformamide → 1-(2-acetyloxyethyl)-N-(3-cyano-4-neopentyloxyphenyl)-5-fluoro-2-methylindole-3-carboxamide

HRID 2216411
Notes
Print preview

Reaction equation

HRID 2216411 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:15][C:16]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([F:27])[CH:25]=3)[NH:20][C:19]=2[CH3:28])=[O:17])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])#[N:2].C(=O)([O-])[O-].[K+].[K+].[C:35]([O:38][CH2:39][CH2:40]Br)(=[O:37])[CH3:36].CN(C)C=O>O>[C:35]([O:38][CH2:39][CH2:40][N:20]1[C:21]2[C:26](=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C:18]([C:16]([NH:15][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:3]([C:1]#[N:2])[CH:4]=2)=[O:17])=[C:19]1[CH3:28])(=[O:37])[CH3:36]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 21058042N-(3-cyano-4-neopentyloxyphenyl)-5-fluoro-2-methyl-1H-indole-3-carboxamide

Product 1

HCID 219423771-(2-acetyloxyethyl)-N-(3-cyano-4-neopentyloxyphenyl)-5-fluoro-2-methylindole-3-carboxamideYield 30.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

N-(3-Cyano-4-neopentyloxyphenyl)-5-fluoro-2-methyl-1H-indole-3-carboxamide ¼ hydrate (0.8 g) obtained in Example 9,. potassium carbonate (0.2 g) and 2-bromoethyl acetate (0.4 g) were added to dimethylformamide (5 ml) and the mixture was stirred at 40° C. for 3 hr. Then the reaction mixture was treated with water and the oganic layer was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was separated and purified by silica gel column chromatography (mobile phase: chloroform) to give the title compound (0.3 g). melting point: 124-125° C.

Workup

  1. extractionthe oganic layer was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe residue was separated
  5. custompurified by silica gel column chromatography (mobile phase: chloroform)

Sources & evidence

ORD record
ord-000fcc7f54a2482fac3279dd1833830d
Source dataset
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07112594B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes