Hydrochloric Acid → HCID 58086135, compound

HRID 1098429Notes

Reaction equation

HRID 1098429 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[CH:19]=3)[N:14]([S:27]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[CH:13]=2)=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[CH:19]=3)[N:14]([S:27]([C:30]3[CH:31]=[CH:32][C:33]([CH3:36])=[CH:34][CH:35]=3)(=[O:29])=[O:28])[CH:13]=2)=[O:11])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58086639HCID 58086639, compound

Product 1

HCID 58086135HCID 58086135, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To (3-nitro-phenyl)-[5-pyridin-3-yl-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone (537, 180 mg, 0.361 mmol) in methanol (4 mL) was added 10% palladium on carbon (20 mg) and few drops of concentrated aqueous hydrochloric acid. The resulting mixture was stirred under an atmosphere of hydrogen overnight and the catalyst was filtered out through a bed of celite. The filtrate was concentrated and purified by silica gel column chromatography eluting with 90% ethyl acetate in hexane to give the compound (538, 58 mg, 34%). MS (ESI) [M+H+]+=469.3.

Workup

  1. filtrationthe catalyst was filtered out through a bed of celite
  2. concentrationThe filtrate was concentrated
  3. custompurified by silica gel column chromatography
  4. washeluting with 90% ethyl acetate in hexane
  5. customto give the compound (538, 58 mg, 34%)

Sources & evidence

ORD record
ord-5a35050453884790a7966abfb445f997
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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