4-(Chloromethyl)pyridinium chloride → HCID 18507782, compound

HRID 1355673Notes

Reaction equation

HRID 1355673 reaction equation
[Br:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][C:7](=[O:23])[N:8]2[CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)=[CH:4][CH:3]=1.Cl.[N:25]1[CH:30]=[CH:29][C:28]([CH2:31]Cl)=[CH:27][CH:26]=1>C1COCC1>[Br:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([C:6]([CH2:31][C:28]3[CH:29]=[CH:30][N:25]=[CH:26][CH:27]=3)([CH2:31][C:28]3[CH:29]=[CH:30][N:25]=[CH:26][CH:27]=3)[C:7](=[O:23])[N:8]2[CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 745704-(Chloromethyl)pyridinium chlorideHCID 18507786HCID 18507786, compound

Product 1

HCID 18507782HCID 18507782, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-7-methyl-1-naphthalen-2-ylmethyl-1,3-dihydro-indol-2-one (495.7 mg, 1.36 mmol) in THF (30 ml) was added 4-picolyl chloride hydrochloride (893 mg, 5.45 mmol). The resulting suspension was purged with nitrogen gas for 10 minutes, after which time an aqueous potassium hydroxide (1N, 10.88 ml, degassed for 10 minutes prior to the addition) was added dropwise at room temperature. The dark solution was stirred at room temperature overnight. After removal of THF, the reaction mixture was partitioned between water and ethyl ether. The organic layer was dried over MgSO4, filtered and concentrated under vacuum to give the crude product. It was chromatographed on flash silica gel eluting with ethyl acetate to provide the title compound of 2D (524 mg, 0.956 mmol, 70.3% yield).

Workup

  1. customThe resulting suspension was purged with nitrogen gas for 10 minutes
  2. customafter which time an aqueous potassium hydroxide (1N, 10.88 ml, degassed for 10 minutes
  3. additionto the addition)
  4. additionwas added dropwise at room temperature
  5. customAfter removal of THF
  6. customthe reaction mixture was partitioned between water and ethyl ether
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customto give the crude product
  11. customIt was chromatographed on flash silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-c9a3eac64cdd4824ad478e76cbcd68b1
Source dataset
uspto-grants-2003_07
Patent number
US06586447B1

Reaction notes

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