2,2-Dimethyl-1,3-dioxane-4,6-dione → 5-[(4-Chloro-2-fluorophenyl){7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 561379

Reaction equation

HRID 561379 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([F:10])[CH:3]=1.[CH3:11][C:12]1([CH3:20])[O:19][C:17](=[O:18])[CH2:16][C:14](=[O:15])[O:13]1.[CH3:21][S:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:32]=1[NH:31][CH:30]=[CH:29]2>C(#N)C.N1CCCC1C(O)=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([C:29]2[C:28]3[C:32](=[C:24]([CH2:23][S:22][CH3:21])[CH:25]=[CH:26][CH:27]=3)[NH:31][CH:30]=2)[CH:16]2[C:17](=[O:18])[O:19][C:12]([CH3:20])([CH3:11])[O:13][C:14]2=[O:15])=[C:4]([F:10])[CH:3]=1

Participants

6

Reactant 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 27249084-Chloro-2-fluorobenzaldehydeHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583924735-[(4-Chloro-2-fluorophenyl){7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dioneYield 92.1%

Reagents, catalysts & solvents 2

HCID 614proline dl-formCatalystHCID 6342AcetonitrileSolvent

Procedure

1.48 g (9.31 mmol) of 4-chloro-2-fluorobenzaldehyde, 1.34 g (9.31 mmol) of Meldrum's acid and 48.7 mg (0.42 mmol) of D,L-proline were added to a solution of 1.50 g (8.46 mmol) of the compound from Example 8A in 70 ml of acetonitrile. The reaction mixture was stirred at RT overnight. It was concentrated, and the residue was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. 3.60 g of the title compound were obtained and were reacted without further purification.

Workup

  1. concentrationIt was concentrated
  2. washwashed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7be1da5f4545427aa7deb9bcf8b38c60
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Linked notes

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