1,1-Dichloroethane → 4-[(6-Chloro-2-fluoropyridin-3-yl)methyl]thiomorpholine 1,1-dioxide

HRID 386016ノート

反応式

HRID 386016 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([F:10])[N:3]=1.ClC(Cl)C.[NH:15]1[CH2:20][CH2:19][S:18](=[O:22])(=[O:21])[CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>>[Cl:1][C:2]1[N:3]=[C:4]([F:10])[C:5]([CH2:6][N:15]2[CH2:20][CH2:19][S:18](=[O:22])(=[O:21])[CH2:17][CH2:16]2)=[CH:8][CH:9]=1

参加物

6

反応物 5

HCID 63651,1-DichloroethaneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 6484228Thiomorpholine 1,1-dioxideHCID 510407866-Chloro-2-fluoronicotinaldehyde

生成物 1

HCID 595257164-[(6-Chloro-2-fluoropyridin-3-yl)methyl]thiomorpholine 1,1-dioxide

実験手順

6-Chloro-2-fluoronicotinaldehyde (116 mg, 0.73 mmol) was added to a 200 mL round bottom under argon. Dichloroethane (2.9 ml) was added followed by thiomorpholine 1,1-dioxide (98 mg, 0.73 mmol). The mixture was stirred for 45 min at room temperature, at which time sodium triacetoxyborohydride (216 mg, 1.02 mmol) was added. The resulting slurry was stirred for 72 hours at room temperature. Saturated aqueous sodium bicarbonate was added and the resulting mixture was extracted twice with ethyl acetate. The combined organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (silica, 0-100% ethyl acetate/hexanes) to afford the title compound.

後処理

  1. additionwas added
  2. extractionthe resulting mixture was extracted twice with ethyl acetate
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by flash chromatography (silica, 0-100% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-ad41fafc84d8448cac19392f4ca0b7d9
出典データセット
uspto-grants-2013_02
特許番号
US08367706B2

反応ノート

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