Hydrochloric Acid → HCID 58086256, compound

HRID 1098432Notes

Reaction equation

HRID 1098432 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:33]=[CH:34][CH:35]=1)[CH2:7][C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:15]=2)[N:10]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:9]=1)([O-])=O.Cl>CO.[Pd]>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:14]2[CH:15]=[C:16]3[C:8]([CH2:7][C:6]4[CH:5]=[C:4]([NH2:1])[CH:35]=[CH:34][CH:33]=4)=[CH:9][N:10]([S:23]([C:26]4[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=4)(=[O:25])=[O:24])[C:11]3=[N:12][CH:13]=2)[CH:18]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58087132HCID 58087132, compound

Product 1

HCID 58086256HCID 58086256, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 3-(3-nitro-benzyl)-5-pyridin-3-yl-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (552, 230 mg, 0.14 mmol) in methanol (5 mL) was added 10% palladium on carbon (10 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 (553, 88 mg, 41%). MS (ESI) [M+H+]+=455.3.

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 (553, 88 mg, 41%)

Sources & evidence

ORD record
ord-573f477164194ad8a7433d480d05bec3
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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