1,8-Diazabicyclo(5.4.0)undec-7-ene → 4H-Pyrano(2,3-b)pyridine, 6-bromo-2-(3,4-dichlorophenyl)-

HRID 280192Notes

Reaction equation

HRID 280192 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:11]=[CH:10][CH:9]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=3)[O:8][C:5]2=[N:6][CH:7]=1.N12CCCN=C1CCCCC2>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:11][CH:10]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=3)[O:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5149096-Bromo-2-(3,4-dichlorophenyl)-2H-pyrano[2,3-b]pyridine

Product 1

HCID 5149104H-Pyrano(2,3-b)pyridine, 6-bromo-2-(3,4-dichlorophenyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.9 g of 6-bromo-2-(3,4-dichlorophenyl)-2H-pyrano[2,3-b]pyridine in 40 ml of tetrahydrofuran was added 0.5 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene. After 1 hour at 25° C., the reaction mixture was partitioned between ethyl acetate and aqueous saturated ammonium chloride solution. The ethyl acetate layer was dried over magnesium sulfate and the solvent was evaporated to leave a solid residue. This was recrystallized from ethanol to give 6-bromo-2-(3,4-dichlorophenyl)-4H-pyrano[2,3-b]pyridine melting at about 138°-139.5° C.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and aqueous saturated ammonium chloride solution
  2. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  3. customthe solvent was evaporated
  4. customto leave a solid residue
  5. customThis was recrystallized from ethanol

Sources & evidence

ORD record
ord-eafa897dc1514dfeadaa3a24cf00cebe
Source dataset
uspto-grants-1986_05
Patent number
US04588733

Reaction notes

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