Pyridine → N-(4-methyl-3-(pyrimidin-5-yl)-phenyl)-9H-fluorene-1-carboxamide

HRID 1835467Notes

Reaction equation

HRID 1835467 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]1[CH:10]=[N:11][CH:12]=[N:13][CH:14]=1.N1C=CC=CC=1.[C:21]1([C:34](Cl)=[O:35])[C:33]2[CH2:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]=2[CH:24]=[CH:23][CH:22]=1>ClCCl>[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:34]([C:21]2[C:33]3[CH2:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:25]=3[CH:24]=[CH:23][CH:22]=2)=[O:35])=[CH:4][C:3]=1[C:9]1[CH:14]=[N:13][CH:12]=[N:11][CH:10]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 255028Fluorene-1-carbonyl chlorideHCID 235036604-Methyl-3-(pyrimidin-5-yl)aniline

Product 1

HCID 23503685N-(4-methyl-3-(pyrimidin-5-yl)-phenyl)-9H-fluorene-1-carboxamideYield 73.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of 4-methyl-3-(pyrimidin-5-yl)aniline (0.111 g) and pyridine (0.15 ml) in dichloromethane (2 ml) was dropwise added a solution of the fluorene-1-carbonyl chloride (0.137 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 triturated with methanol. The resulting solid was collected by filtration to give N-(4-methyl-3-(pyrimidin-5-yl)-phenyl)-9H-fluorene-1-carboxamide (0.167 g, 73.9%)

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 triturated with methanol
  5. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-9e4636e5e4334990a367db70e3b23575
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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