Pyridine → N-[3-(pyrimidin-5-yl)phenyl]fluorene-1-carboxamide

HRID 1835436Notes

Reaction equation

HRID 1835436 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]([CH:11]=[CH:12][CH:13]=2)[NH2:10])[CH:4]=[N:3][CH:2]=1.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]=[C:5]([C:7]2[CH:8]=[C:9]([NH:10][C:33]([C:20]3[C:32]4[CH2:31][C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[C:24]=4[CH:23]=[CH:22][CH:21]=3)=[O:34])[CH:11]=[CH:12][CH:13]=2)[CH:4]=[N:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 255028Fluorene-1-carbonyl chlorideHCID 71620493-Pyrimidin-5-ylaniline

Product 1

HCID 9820411N-[3-(pyrimidin-5-yl)phenyl]fluorene-1-carboxamideYield 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of 3-(pyrimidin-5-yl)aniline (0. 17g) 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 (5 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. The residue was purified by a silica gel column chromatography eluting with 2% methanol in dichloromethane to give N-[3-(pyrimidin-5-yl)phenyl]fluorene-1-carboxamide (0.222 g, 61.2 %).

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
  4. customThe residue was purified by a silica gel column chromatography
  5. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-a3d307b522294413b85324954a1e0795
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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