3,4-dihydro-2H-pyran → HCID 59582216, compound

HRID 2061294Notes

Reaction equation

HRID 2061294 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.[O:16]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17]1.C([O-])(O)=O.[Na+]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.ClCCl>[Br:15][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21][O:16]3)[C:5]3[C:13]([C:12]=2[CH:11]=1)=[CH:14][C:2]([Br:1])=[CH:3][CH:4]=3

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 2748743,6-DibromocarbazoleHCID 516892Sodium Bicarbonate

Product 1

HCID 59582216HCID 59582216, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a flask (1 L) under N2 at room temperature, were added 3,6-dibromocarbazole (50 g), dichloromethane (500 mL), 3,4-dihydro-2H-pyran (40 g), p-toluenesulfonic acid monohydrate (1 g). The reaction was stirred overnight. NaHCO3 (3 g) was added, and the reaction was stirred for 1 h. After filtration, the solvent in the filtrate was removed by evaporation. MeOH (1 L) was added for reflux under N2 for 2 h. Filtration when it was warm gave 37.5 g product. The MeOH (800 mL) was removed by evaporation, and solid came out. Filtration gave 12.5 g product. Both products are white, single spot on TLC, and GS-MS and 1H NMR showed they are pure product. The overall yield is 80%. Second and Third Reactions following the reaction scheme above produce compound (2) and (3), respectively, according to the scheme below:

Workup

  1. stirringthe reaction was stirred for 1 h
  2. filtrationAfter filtration
  3. customthe solvent in the filtrate was removed by evaporation
  4. additionMeOH (1 L) was added
  5. temperaturefor reflux under N2 for 2 h
  6. filtrationFiltration when it
  7. temperaturewas warm

Sources & evidence

ORD record
ord-a5218e24588a42a0b3f55e7085ee7600
Source dataset
uspto-grants-2012_10
Patent number
US08283002B2

Reaction notes

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