Hydrochloric Acid → {3-[(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-carbamic acid benzyl ester

HRID 217586노트

반응식

HRID 217586 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[OH-].[K+].[CH2:13]([O:20][C:21](=[O:33])[NH:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[C:25]([CH:30]=[O:31])[C:24]=1[F:32])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>CO>[CH2:13]([O:20][C:21](=[O:33])[NH:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[C:25]([CH:30]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[NH:8][CH:9]=2)[OH:31])[C:24]=1[F:32])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 242292135-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 58086235Benzyl (2,4-difluoro-3-formylphenyl)carbamate

생성물 1

HCID 58087936{3-[(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-carbamic acid benzyl ester수율 46.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Into a round bottom flask was added 5-chloro-1H-pyrrolo[2,3-b]pyridine (5, 0.524 g, 3.43 mmol) in 5.00 mL of methanol. Potassium hydroxide (0.800 g, 14.2 mmol) and (2,4-difluoro-3-formyl-phenyl)-carbamic acid benzyl ester (4, 1.02 g, 3.5 mmol) were added and the reaction mixture was stirred overnight. The reaction mixture was poured into 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum and crystallized from ethyl acetate to give the desired compound (6, 710 mg, 46%). MS (ESI) [M+H+]+=444.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. customcrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-f0a4874354a84b36a3e833bf34a2ca59
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198273B2

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