Sodium cyanoborohydride → 1H-Indole, 4-(difluoromethoxy)-2,3-dihydro-

HRID 2278658노트

반응식

HRID 2278658 반응식
C([BH3-])#N.[Na+].[F:5][CH:6]([F:17])[O:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[CH:11][NH:12]2>FC(F)(F)C(O)=O>[F:17][CH:6]([F:5])[O:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH2:10][CH2:11][NH:12]2

참가 물질

4

반응물 2

HCID 5003444Sodium cyanoborohydrideHCID 866992854-(difluoromethoxy)-1H-indole

생성물 1

HCID 866992831H-Indole, 4-(difluoromethoxy)-2,3-dihydro-수율 29.7%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

반응 조건

온도
0 °C

실험 절차

0.722 mg of sodium cyanoborohydride is added to a solution of 1 g of 4-difluoromethoxy-1H-indole in 15 ml of trifluoroacetic acid, cooled to 0° C., and the stirring is continued for 3 hours. The reaction mixture is then concentrated under reduced pressure, treated with a concentrated sodium hydroxide solution, extracted with dichloromethane, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica column chromatography, elution being carried out with a mixture of heptane and ethyl acetate (20/80: v/v), so as to give 300 mg of 4-difluoromethoxy-2,3-dihydro-1H-indole in the form of a yellow oil, the characteristics of which are the following:

후처리

  1. concentrationThe reaction mixture is then concentrated under reduced pressure
  2. additiontreated with a concentrated sodium hydroxide solution
  3. extractionextracted with dichloromethane
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica column chromatography, elution
  8. additionbeing carried out with a mixture of heptane and ethyl acetate (20/80: v/v)

출처 및 근거

ORD 기록
ord-4bb71e9b6e0d4e118bd5b6c79c75b6f8
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133168B2

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