Methanol → 8-fluoro-7-trifluoromethyl-3,4-dihydro-2H-isoquinolin-1-one

HRID 1844042노트

반응식

HRID 1844042 반응식
[N-:1]=[N+]=[N-].[Na+].[F:5][C:6]1[C:7]([C:16]([F:19])([F:18])[F:17])=[CH:8][CH:9]=[C:10]2[C:14]=1[C:13](=[O:15])[CH2:12][CH2:11]2.CO>C(O)(C(F)(F)F)=O.C(Cl)(Cl)Cl>[F:5][C:6]1[C:7]([C:16]([F:19])([F:18])[F:17])=[CH:8][CH:9]=[C:10]2[C:14]=1[C:13](=[O:15])[NH:1][CH2:12][CH2:11]2

참가 물질

6

반응물 3

HCID 887MethanolHCID 33557Sodium AzideHCID 668036517-fluoro-6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-one

생성물 1

HCID 668020098-fluoro-7-trifluoromethyl-3,4-dihydro-2H-isoquinolin-1-one수율 56.1%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6422Trifluoroacetic acid용매

실험 절차

Sodium azide (492 mg, 7.5688 mmol) was added portion wise to a stirred solution of 7-fluoro-6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-one (I-77c: 500 mg, 2.2935 mmol) in TFA (15 mL) over a period of 5 hours at 80° C. The reaction was monitored by TLC (5% methanol in CHCl3). The reaction mixture was concentrated under reduced pressure, followed by the addition of ice. The precipitated solid was filtered, washed with water (20 mL) and dried under reduced pressure to yield the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3) afforded 300 mg of the product (56.1% yield).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionfollowed by the addition of ice
  3. filtrationThe precipitated solid was filtered
  4. washwashed with water (20 mL)
  5. customdried under reduced pressure
  6. customto yield the crude product
  7. customPurification by column chromatography on silica gel (2% methanol in CHCl3)

출처 및 근거

ORD 기록
ord-66240a63a9f14aa29336f30e9a86d8d7
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946260B2

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