Potassium Carbonate → HCID 18415768, compound

HRID 991001Notes

Reaction equation

HRID 991001 reaction equation
[NH:1]1[C:5]2[C:6]3[C:11]([CH2:12][C:4]=2[C:3]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[N:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3.C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][C:28]([NH2:30])=[O:29]>CN(C)C=O.ClCCl>[NH:1]1[C:5]2[C:6]3[C:11]([CH2:12][C:4]=2[C:3]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:27][C:28]([NH2:30])=[O:29])=[CH:15][CH:14]=2)=[N:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 135512470HCID 135512470, compound

Product 1

HCID 18415768HCID 18415768, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenol (0.28 g, Example 30), potassium carbonate (0.16 g) and 2-bromoacetamide (0.16 g) was stirred together at ambient temperature in dry dimethyl formamide (5 ml) for 4 days and then allowed to stand at ambient temperature for 9 days. The mixture was diluted with dichloromethane (50 ml) and washed with 1M aqueous sodium hydroxide solution and then with water. Some insoluble material which remained throughout the extractions was collected by filtration. The solid was purified by flash column chromatography on silica using ethyl acetate as the mobile phase. Appropriate fractions were collected, combined and evaporated to give 2-[4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenoxy]acetamide, m.p. 247-248° C.

Workup

  1. washwashed with 1M aqueous sodium hydroxide solution
  2. extractionSome insoluble material which remained throughout the extractions
  3. filtrationwas collected by filtration
  4. customThe solid was purified by flash column chromatography on silica
  5. customAppropriate fractions were collected
  6. customevaporated

Sources & evidence

ORD record
ord-b03e9e334f874791a261999fd7aa6944
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

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