Pyridine → N-(3-(pyridin-3-yl)phenyl)-9H-fluorene-1-carboxamide

HRID 1835435Notes

Reaction equation

HRID 1835435 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:14]1([C:27](Cl)=[O:28])[C:26]2[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]=2[CH:17]=[CH:16][CH:15]=1>ClCCl>[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:4]2[CH:3]=[C:2]([NH:1][C:27]([C:14]3[C:26]4[CH2:25][C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[C:18]=4[CH:17]=[CH:16][CH:15]=3)=[O:28])[CH:7]=[CH:6][CH:5]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6115AnilineHCID 255028Fluorene-1-carbonyl chloride

Product 1

HCID 23503668N-(3-(pyridin-3-yl)phenyl)-9H-fluorene-1-carboxamideYield 87.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of 3-pyridin-3-yl)aniline (0.17 g) and pyridine (0.24 ml) in dichloromethane (3 ml) was dropwise added a solution of the fluorene-1-carbonyl chloride (0.23 g) in dichloromethane (2 ml) followed by stirring for 2 hours. The mixture was diluted with dichloromethane and washed with an aqueous solution of sodium hydrogen carbonate and brine. The separated organic layer was dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by a silica gel column chromatography eluting with 2% methanol in dichloromethane to give N-(3-(pyridin-3-yl)phenyl)-9H-fluorene-1-carboxamide (0.317 g, 87.6%).

Workup

  1. washwashed with an aqueous solution of sodium hydrogen carbonate and brine
  2. dry with materialThe separated organic layer was dried over sodium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by a silica gel column chromatography
  5. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-f5bc89524026440a8aa315c707dd2bb3
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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