Hydrochloric Acid → HCID 453412, compound

HRID 864438Notes

Reaction equation

HRID 864438 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH2:14][N:15]([CH3:25])[C:16]1[C:21]([N+:22]([O-])=O)=[CH:20][CH:19]=[CH:18][N:17]=1)=[O:11].[C:26]([BH3-])#N.[Na+].Cl.[OH-].[Na+].[CH2:33](O)[CH3:34]>CO.[Pd].C(O)(=O)C.CC(C)=O>[CH3:25][N:15]([CH2:14][CH2:13][O:12][C:10]([C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:11])[C:16]1[C:21]([NH:22][CH:33]([CH3:34])[CH3:26])=[CH:20][CH:19]=[CH:18][N:17]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydride2×HCID 19418859HCID 19418859, compound

Product 1

HCID 453412HCID 453412, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

Palladium black (110 mg) is added to 2-(N-methyl-N-(3-nitro-2-pyridinyl)amino)-ethyl indol-2-carboxylate (PREPARATION 37, 195 mg) in methanol (75 ml). The mixture is stirred under a hydrogen atmosphere (balloon) for 30 min at 20°-25°, filtered and concentrated to give a solid. The solid is dissolved in ethanol (12 ml) and treated with acetone (0.64 ml) and sodium cyanoborohydride (27 mg). Acetic acid is added to adjust to pH 5 as measured on moistened pH test paper. The mixture is stirred for 3.8 days during which time additional sodium cyanoborohydride (39 mg) is added in portions, adjusting the pH on each addition. The mixture is adjusted to pH 3 with aqueous hydrochloric acid (10), neutralized with aqueous sodium hydroxide (5%) and concentrated under reduced pressure to 5 ml. The residue is diluted with chloroform, washed with water, saturated aqueous potassium carbonate, saline and dried over magnesium sulfate. Removal of solvent under reduced pressure gives an oil which is chromatographed on silica gel (10 g, 230-400 mesh) eluting with a gradient of 10-50% ethyl acetate/hexane. The appropriate fractions are pooled and concentrated to give the title compound, mp 130°-131°.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customto give a solid
  4. additionis added in portions
  5. additionon each addition
  6. concentrationconcentrated under reduced pressure to 5 ml
  7. additionThe residue is diluted with chloroform
  8. washwashed with water, saturated aqueous potassium carbonate, saline
  9. dry with materialdried over magnesium sulfate
  10. customRemoval of solvent under reduced pressure
  11. customgives an oil which
  12. customis chromatographed on silica gel (10 g, 230-400 mesh)
  13. washeluting with a gradient of 10-50% ethyl acetate/hexane
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-18e2a2eed5d14bf7be45ebb759346ca4
Source dataset
uspto-grants-1996_10
Patent number
US05563142

Reaction notes

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