Acetic Acid → HCID 86628684, compound

HRID 2079909Notes

Reaction equation

HRID 2079909 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:16]=3)[N:11]([CH:23]([CH3:25])[CH3:24])[CH:10]=2)=[CH:5][CH:4]=1)#N.C(O)(=[O:28])C.N1C=CC=CC=1>[Ni].O>[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:16]=3)[N:11]([CH:23]([CH3:25])[CH3:24])[CH:10]=2)=[CH:5][CH:4]=1)=[O:28]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 1049PyridineHCID 24739997HCID 24739997, compound

Product 1

HCID 86628684HCID 86628684, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

Method Z-1 Place N-[3-(4-Cyano-phenyl)-1-isopropyl-1H-indol-6-yl]-methanesulfonamide (500 mg, 1.41 mmol), sodium hyposulfite hydrate (311 mg, 3.53 mmol) and Raney nickel (50% soln in water, 700 μL, 2.96 mmol) in a round bottom flask then add water (6 mL), glacial acetic acid (12 mL) and pyridine (12 mL). Warm to 50° C., and stir for 1.5 hours. Cool to ambient temperature; dilute with water (10 mL); and extract with ethyl acetate (10 mL×3). Combine organic layers, and wash with saturated sodium bicarbonate, water (×3) and brine. Dry over sodium sulfate, and concentrate in vacuo. Purify residue by flash chromatography on silica (2-50% ethyl acetate in hexanes) to give N-[3-(4-formyl-phenyl)-1-isopropyl-1H-indol-6-yl]-methanesulfonamide (413.1 mg, 82%). LRMS (API ES−)=355.0 (M−H).

Workup

  1. temperatureCool to ambient temperature
  2. extractionand extract with ethyl acetate (10 mL×3)
  3. washCombine organic layers, and wash with saturated sodium bicarbonate, water (×3) and brine
  4. dry with materialDry over sodium sulfate
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-b99dbb7233ad475d8815a830329db832
Source dataset
uspto-grants-2011_04
Patent number
US07932284B2

Reaction notes

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