Hydrochloric Acid → HCID 57891759, compound

HRID 1820908Notes

Reaction equation

HRID 1820908 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[C:12]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27]CC4C=CC=CC=4)[CH:20]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1.CO.Cl>[Pd]>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[C:12]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([OH:27])[CH:20]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8028TetrahydrofuranHCID 57891692HCID 57891692, compound

Product 1

HCID 57891759HCID 57891759, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Into a Parr pressure reactor 1-Benzenesulfonyl-3-(3-benzyloxy-4-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine (92 mg, 0.00020 mol) was placed with Palladium (50 mg, 0.00005 mol) 10%, tetrahydrofuran (15 mL, 0.18 mol) and Methanol (1 mL, 0.02 mol) and HCl solution (3 mL, 0.04 mol). The reaction was shaken under an atmosphere of hydrogen at 50 psi for 4 hours. The mixture reaction was filtered through Celite™ and concentrated under reduced pressure. The residue was purified by preparative TLC (ethyl acetate/hexanes 1:1) to give 31 mg of the titled product. MS(ESI) [M+H+]+=381.11.

Workup

  1. customThe mixture reaction
  2. filtrationwas filtered through Celite™
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by preparative TLC (ethyl acetate/hexanes 1:1)

Sources & evidence

ORD record
ord-bf3ab16831be4b48a878307f3ed208dd
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Reaction notes

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