[3-benzyloxy-2-cyclopropylmethoxy-phenyl]-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone → (5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-(2-cyclopropylmethoxy-3-hydroxy-phenyl)-methanone

HRID 253453Notes

Reaction equation

HRID 253453 reaction equation
C([O:8][C:9]1[C:10]([O:27][CH2:28][CH:29]2[CH2:31][CH2:30]2)=[C:11]([C:15]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[C:23]([Cl:26])[CH:24]=3)[NH:19][CH:18]=2)=[O:16])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>[Pd].CO.O1CCCC1>[Cl:26][C:23]1[CH:24]=[C:25]2[C:17]([C:15]([C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[C:10]=3[O:27][CH2:28][CH:29]3[CH2:31][CH2:30]3)=[O:16])=[CH:18][NH:19][C:20]2=[N:21][CH:22]=1

Participants

5

Reactant 1

HCID 59803895[3-benzyloxy-2-cyclopropylmethoxy-phenyl]-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

Product 1

HCID 59803815(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-(2-cyclopropylmethoxy-3-hydroxy-phenyl)-methanoneYield 32.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [3-benzyloxy-2-cyclopropylmethoxy-phenyl]-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone (132, 0.92 g, 2.13 mmol) and palladium on carbon (100 mg, 10%, 0.5 mmol) in methanol (60 mL) and tetrahydrofuran (60 mL) was stirred under an atmosphere of hydrogen overnight. After filtering off of catalyst and removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexane to provide the compound as a white solid (133, 236 mg, 32%).

Workup

  1. filtrationAfter filtering off of catalyst and removal of solvent
  2. customthe residue was purified by silica gel column chromatography
  3. washeluting with ethyl acetate in hexane

Sources & evidence

ORD record
ord-43745005e48948c5bac6d55aa50de4da
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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