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

HRID 249817

反応式

HRID 249817 の反応式
Cl[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.CO.[OH-].[K+].[CH2:15]([O:22][C:23](=[O:35])[NH:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[C:27]([CH:32]=[O:33])[C:26]=1[F:34])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>>[CH2:15]([O:22][C:23](=[O:35])[NH:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[C:27]([CH:32]([OH:33])[C:10]2[C:4]3[C:5](=[N:6][CH:7]=[CH:2][CH:3]=3)[NH:8][CH:9]=2)[C:26]=1[F:34])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

6

反応物 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 242292135-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 58086235Benzyl (2,4-difluoro-3-formylphenyl)carbamate

生成物 1

HCID 66679278{2,4-difluoro-3-[hydroxy-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-phenyl}-carbamic acid benzyl ester収率 50.6%

実験手順

Into a round bottom flask was added 5-chloro-1-pyrrolo[2,3-b]pyridine (6, 0.524 g, 3.43 mmol, prepared as described in Example 5) in methanol (5.00 mL, 0.123 mol). Potassium hydroxide (0.800 g, 14.2 mmol) and (2,4-difluoro-3-formyl-phenyl)-carbamic acid benzyl ester (53, 1.02 g, 3.5 mmol) were added and the reaction mixture was stirred overnight. The reaction mixture was poured into 1N HCl and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated and crystallized from ethyl acetate to give compound 54 (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. concentrationconcentrated
  5. customcrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-597c4724684e4fcfb69cb29bb8609a82
出典データセット
uspto-grants-2011_01
特許番号
US07863289B2

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