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

HRID 2173051ノート

反応式

HRID 2173051 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 15413tert-Butyl methyl ether溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ae7a6c7c50ad4df1b6b1577d342e8b20
出典データセット
uspto-grants-2015_06
特許番号
US09056873B2

反応ノート

読み込み中…