Hydrochloric Acid → HCID 58086256, compound

HRID 1261069Notes

Reaction equation

HRID 1261069 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-84e538d2e80149b88c7b47f8b14fa8f2
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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