Pyridine → N-(3-(pyrazin-2-yl)phenyl)-9H-fluorene-1-carboxamide

HRID 1835443Notes

Reaction equation

HRID 1835443 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9]([CH:11]=[CH:12][CH:13]=1)[NH2:10].N1C=CC=CC=1.[C:20]1([C:33](Cl)=[O:34])[C:32]2[CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]=2[CH:23]=[CH:22][CH:21]=1>ClCCl>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9]([NH:10][C:33]([C:20]2[C:32]3[CH2:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:24]=3[CH:23]=[CH:22][CH:21]=2)=[O:34])[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 255028Fluorene-1-carbonyl chlorideHCID 235036723-(Pyrazin-2-yl)aniline

Product 1

HCID 23503682N-(3-(pyrazin-2-yl)phenyl)-9H-fluorene-1-carboxamideYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of 3-(pyrazin-2-yl)aniline (0.12g) and pyridine (0.17ml) in dichloromethane (3ml) was dropwise added a solution of the fluorene-1-carbonyl chloride (0.16 g) in dichloromethane (3 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-(pyrazin-2-yl)phenyl)-9H-fluorene-1-carboxamide (0.193 g; 76.0%).

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-2158a663affa414a94039e6fe35970a5
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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