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

HRID 1261086Notes

Reaction equation

HRID 1261086 reaction equation
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

Participants

6

Reactant 5

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

Product 1

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

Procedure

Into a round bottom flask was added 5-chloro-1H-pyrrolo[2,3-b]pyridine (80, 0.524 g, 3.43 mmol, prepared as described in Example 9) 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 (614, 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 615 (710 mg, 46%). MS (ESI) [M+H+]+=444.

Workup

  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

Sources & evidence

ORD record
ord-6d213514aead450d8ffde59b7a057be1
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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