Trifluoroacetic acid → 4-Chloro-6,7-difluoro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one

HRID 2173051노트

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HRID 2173051 반응식
[Cl:1][C:2]1[C:7]2[C:8](=[O:12])[NH:9][CH:10](O)[C:6]=2[C:5]([F:13])=[C:4]([F:14])[N:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>CC(OC)(C)C>[Cl:1][C:2]1[C:7]2[C:8](=[O:12])[NH:9][CH2:10][C:6]=2[C:5]([F:13])=[C:4]([F:14])[N:3]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 867272474-Chloro-6,7-difluoro-1-hydroxy-1H-pyrrolo[3,4-c]pyridin-3(2H)-one

생성물 1

HCID 867272484-Chloro-6,7-difluoro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one수율 82%

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매

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온도
60 °C

실험 절차

To an inert 50 mL round bottom flask with magnetic stirring was added 4-chloro-6,7-difluoro-1-hydroxy-1H-pyrrolo[3,4-c]pyridin-3(2H)-one (4.39 g, 19.90 mmol) and trifluoroacetic acid (18.40 mL, 239 mmol). The solids were suspended with stirring and triethylsilane (7.95 mL, 49.8 mmol) was added. The reaction mixture was heated to 60° C. and stirred for 30 minutes at that temperature. The reaction mixture was subsequently cooled to room temperature and added dropwise to MTBE (88 mL) to produce a white precipitate. The suspension was cooled to 5° C. for 45 minutes. The solids were filtered, washed with MTBE (20 mL) and air dried on the filter to afford the title compound (3.336 g, 82%). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.58 (s, 2H), 9.13 (s br, 1H).

후처리

  1. stirringwith stirring
  2. stirringstirred for 30 minutes at that temperature
  3. temperatureThe reaction mixture was subsequently cooled to room temperature
  4. customto produce a white precipitate
  5. temperatureThe suspension was cooled to 5° C. for 45 minutes
  6. filtrationThe solids were filtered
  7. washwashed with MTBE (20 mL) and air
  8. customdried on the
  9. filtrationfilter

출처 및 근거

ORD 기록
ord-ae7a6c7c50ad4df1b6b1577d342e8b20
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056873B2

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