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

HRID 2361745Notes

Reaction equation

HRID 2361745 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, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4-bromo-2-chloro-phenylamine (0.5 g, 2.422 mmol), tetrahydropyran-4-one (1.308 ml, 10.898 mmol), and sodium triacetoxyborohydride (2.31 g, 10.898 mmol) in DCE (20 ml) was stirred at room temperature for 16 h. The reaction mixture was washed with NaHCO3 (aqueous sat. solution), dried (Na2SO4) and the solvent was evaporated in vacuo. The residue was purified by column chromatography (silica gel; heptane/DCM up to 40% as eluent). The desired fractions were collected and evaporated in vacuo to yield compound D13 (0.383 g, 52%) as white solid.

Workup

  1. washThe reaction mixture was washed with NaHCO3 (aqueous sat. solution)
  2. dry with materialdried (Na2SO4)
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was purified by column chromatography (silica gel; heptane/DCM up to 40% as eluent)
  5. customThe desired fractions were collected
  6. customevaporated in vacuo
  7. customto yield compound D13 (0.383 g, 52%) as white solid

Sources & evidence

ORD record
ord-f2a4bc3c2b4448eaa08b1690e564a28b
Source dataset
uspto-grants-2014_04
Patent number
US08691813B2

Reaction notes

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