2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 58392263, compound

HRID 561380Notes

Reaction equation

HRID 561380 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.[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]([F:10])[CH:3]=1

Participants

6

Reactant 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 27249084-Chloro-2-fluorobenzaldehydeHCID 583922275-Fluoro-7-[(methylsulfanyl)methyl]-1H-indole

Product 1

HCID 58392263HCID 58392263, compoundYield 103.9%

Reagents, catalysts & solvents 2

HCID 614proline dl-formCatalystHCID 6342AcetonitrileSolvent

Procedure

0.70 g (4.41 mmol) of 4-chloro-2-fluorobenzaldehyde, 0.64 g (4.41 mmol) of Meldrum's acid and 24 mg (0.21 mmol) of D,L-proline were added to a solution of 1.00 g of the compound of 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. 2.20 g of the title compound were obtained with a purity of 71% (78% of theory) 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-26431e6a4a6c4a25a011ddb335f4ea16
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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