Hydrochloric Acid → HCID 58173248, compound

HRID 1191902Notes

Reaction equation

HRID 1191902 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([CH3:20])=[CH:17][CH:18]=3)[C:13]([CH:21]=[O:22])=[CH:12]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:23]([O-:25])=[O:24].[BH4-].[Na+].Cl>CO.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([CH3:20])=[CH:17][CH:18]=3)[C:13]([CH2:21][OH:22])=[CH:12]2)(=[O:9])=[O:10])=[CH:4][C:3]=1[N+:23]([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86651735HCID 86651735, compound

Product 1

HCID 58173248HCID 58173248, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To the solution of 1-(4-chloro-3-nitro-benzenesulfonyl)-5-methyl-1H-indole-3-carbaldehyde (284.10 mg, 0.75 mmol) in the mixture of methanol/THF (1:1, 20 mL), NaBH4(32 mg, 0.825 mmol) was added slowly at 0° C. After addition, the reaction was stirred for additional 30 min at same temperature. 1.0 ml of 1N HCl was added after reaction was completed, as determined by checking using thin layer chromatography (TLC). The resulting reaction mixture was concentrated, and the residue was diluted with water (20 ml) and extracted with ethyl acetate (3×10 ml). The combined organic layers was washed with water, 10% NaHCO3, and brine, dried with MgSO4, filtered and concentrated. The residue was purified with column chromatography to give pure product, OSU-A9M (248.5 mg, 87%) as off white solid.

Workup

  1. additionwas added slowly at 0° C
  2. additionAfter addition
  3. customafter reaction
  4. customThe resulting reaction mixture
  5. concentrationwas concentrated
  6. additionthe residue was diluted with water (20 ml)
  7. extractionextracted with ethyl acetate (3×10 ml)
  8. washThe combined organic layers was washed with water, 10% NaHCO3, and brine
  9. dry with materialdried with MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified with column chromatography
  13. customto give pure product, OSU-A9M (248.5 mg, 87%) as off white solid

Sources & evidence

ORD record
ord-12e7503f106a4489bacb623c229b6f3d
Source dataset
uspto-grants-2014_03
Patent number
US08680133B2

Reaction notes

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