Pyridine → phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone O-benzyloxime hydrochloride

HRID 1821892Notes

Reaction equation

HRID 1821892 reaction equation
[C:1]1([C:7]([C:9]2[N:17](S(C3C=CC=CC=3)(=O)=O)[C:12]3=[CH:13][N:14]=[CH:15][CH:16]=[C:11]3[CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:27].[CH2:28]([O:35][NH2:36])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.N1C=CC=CC=1.[NH4+].[Cl-]>ClCCCl>[ClH:27].[CH2:28]([O:35][N:36]=[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:9]1[NH:17][C:12]2=[CH:13][N:14]=[CH:15][CH:16]=[C:11]2[CH:10]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 25517Ammonium ChlorideHCID 102312Benzyloxyamine hydrochlorideHCID 689825291h-Pyrrolo[2,3-c]pyridine,2-benzoyl-1-(phenylsulfonyl)-

Product 1

HCID 136366029phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone O-benzyloxime hydrochlorideYield 47%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of phenyl[1-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridin-2-yl]methanone (Reference Example 13) (200 mg, 0.55 mmol), O-benzylhydroxylamine hydrochloride (97 mg, 0.92 mmol) and pyridine (74 μL, 0.92 mmol) in 1,2-dichloroethane (8 mL) was heated at 60° C. After 24 h, saturated NH4Cl (10 mL) was added and the mixture was extracted with EtOAc (2×25 mL). The combined extracts were washed with saturated NaCl (20 mL), dried (Na2SO4) and concentrated under reduced pressure. Purification by column chromatography (silica gel, 1:1 hexanes/EtOAc) gave phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone O-benzyloxime hydrochloride (84 mg, 47%) as a mixture of isomers: mp 153-155° C.; 1H NMR (500 MHz, DMSO-d6) δ 5.35-5.40 (2H, m), 6.66 (0.5H, s), 7.12 (0.5H, s), 7.34-7.56 (10H, m), 8.07 (0.5H, d, J=6.3 Hz), 8.19 (0.5H, d, J=6.3 Hz), 8.29 (0.5H, d, J=6.3 Hz), 8.34 (0.5H, d, J=6.3 Hz), 8.99 (0.5H, s), 9.17 (0.5H, s), 13.04 (0.5H, s), 13.14 (0.5H, s), 15.14 (1H, br s); ESI MS m/z 328 [C21H17N3O+H]+; HPLC (Method A) 98.3% (AUC), tR=19.1 and 19.3 min.

Workup

  1. extractionthe mixture was extracted with EtOAc (2×25 mL)
  2. washThe combined extracts were washed with saturated NaCl (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by column chromatography (silica gel, 1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-a3654da889f7491c9e669169983c5a75
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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