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

反応式

HRID 561379 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 614proline dl-form触媒HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7be1da5f4545427aa7deb9bcf8b38c60
出典データセット
uspto-grants-2011_11
特許番号
US08063234B2

関連ノート

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