Tetrahydro-4H-pyran-4-one → HCID 43608624, compound

HRID 1020853Notes

Reaction equation

HRID 1020853 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([Cl:9])[CH:3]=1.[O:10]1[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:13]2[CH2:14][CH2:15][O:10][CH2:11][CH2:12]2)=[C:4]([Cl:9])[CH:3]=1

Participants

5

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 6101694-Bromo-2-chloroanilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 43608624HCID 43608624, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4-bromo-2-chloro-phenylamine (4 g, 19.37 mmol), tetrahydro-4H-pyran-4-one (2.69 ml, 29.05 mmol), oven-dried molecular sieves 4 Å (2 g) and sodium triacetoxyborohydride (6.12 g, 29.05 mmol) in DCE (100 ml) was stirred at r.t. for 72 h. The mixture was filtered through a pad of diatomaceous earth. The diatomaceous earth pad was then washed with DCM. The combined filtrates were washed with NaHCO3 (aqueous saturated solution), dried (Na2SO4) and concentrated in vacuo. The crude product thus obtained was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 5%). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D32 as a brown oil (4.83 g, 86%).

Workup

  1. filtrationThe mixture was filtered through a pad of diatomaceous earth
  2. washThe diatomaceous earth pad was then washed with DCM
  3. washThe combined filtrates were washed with NaHCO3 (aqueous saturated solution)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product thus obtained
  7. customwas purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 5%)
  8. customThe desired fractions were collected
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c89f313fac9c4934b7cb802025030c76
Source dataset
uspto-grants-2014_05
Patent number
US08716480B2

Reaction notes

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