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

HRID 217586ノート

反応式

HRID 217586 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f0a4874354a84b36a3e833bf34a2ca59
出典データセット
uspto-grants-2012_06
特許番号
US08198273B2

反応ノート

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