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

HRID 386016노트

반응식

HRID 386016 반응식
[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

참가 물질

6

반응물 5

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

생성물 1

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

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ad41fafc84d8448cac19392f4ca0b7d9
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

반응 노트

불러오는 중…