4-Azafluorene → HCID 10545749, compound

HRID 1463686Notes

Reaction equation

HRID 1463686 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[N:4]=[CH:3][CH:2]=1.[H-].[Na+].[N:16]1[CH:21]=[CH:20][C:19]([CH2:22]Cl)=[CH:18][CH:17]=1>C(OCC)(=O)C>[N:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:12]2([CH2:22][C:19]3[CH:20]=[CH:21][N:16]=[CH:17][CH:18]=3)[C:13]3[C:5](=[N:4][CH:3]=[CH:2][CH:1]=3)[C:6]3[C:11]2=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 92054-AzafluoreneHCID 24758Sodium hydrideHCID 745714-(Chloromethyl)pyridine

Product 1

HCID 10545749HCID 10545749, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following the procedure described in Example 608, Part D, alkylation of 2.1 g (12.6 mole) of 4-azafluorene, in the presence of 1.51 g (31.45 mmole) of 50% sodium hydride with 5.0 g (30.4 mmole) of 4-picolyl-chloride yielded 2.8 g. Flash chromatography with ethyl acetate yielded 2.0 g of material containing a small amount of color. Recrystallization from butyl chloride yielded 1.5 g of pure compound, m.p. 163°-4°.

Workup

  1. customyielded 2.8 g

Sources & evidence

ORD record
ord-a2b8177ebd0345a8b3d409f73da7e7f6
Source dataset
uspto-grants-1994_04
Patent number
US05300642

Reaction notes

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