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

HRID 561429Notes

Reaction equation

HRID 561429 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([CH3:10])[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.[F:21][C:22]1[CH:23]=[C:24]2[C:28](=[C:29]([CH2:31][S:32][CH3:33])[CH:30]=1)[NH:27][CH:26]=[CH:25]2>C(#N)C.N1CCCC1C(O)=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([C:25]2[C:24]3[C:28](=[C:29]([CH2:31][S:32][CH3:33])[CH:30]=[C:22]([F:21])[CH:23]=3)[NH:27][CH:26]=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]([CH3:10])[CH:3]=1

Participants

6

Reactant 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 27576584-Chloro-2-methylbenzaldehydeHCID 583922275-Fluoro-7-[(methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583923015-[(4-Chloro-2-methylphenyl){5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dioneYield 114.3%

Reagents, catalysts & solvents 2

HCID 614proline dl-formCatalystHCID 6342AcetonitrileSolvent

Procedure

0.68 g (4.41 mmol) of 4-chloro-2-methylbenzaldehyde, 0.64 g (4.41 mmol) of Meldrum's acid and 24.0 mg (0.21 mmol) of D,L-proline were added to a solution of 1.00 g of the compound from Example 11A with a purity of 82% (4.20 mmol) in 35 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 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution and water, dried over magnesium sulfate, filtered and concentrated. 2.40 g of the title compound were obtained and were reacted without further purification.

Workup

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

Sources & evidence

ORD record
ord-841f5d7f1a3347af9212298297445186
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

Loading…