Ethanol → HCID 76540061, compound

HRID 2079910Notes

Reaction equation

HRID 2079910 reaction equation
[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.Cl.[NH2:27][OH:28].C(O)C.O1CCCC1>C(OCC)(=O)C.N1C=CC=CC=1>[OH:28][N:27]=[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

Participants

7

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 443297Hydroxyamine hydrochlorideHCID 86628684HCID 86628684, compound

Product 1

HCID 76540061HCID 76540061, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Method Z-2 Place N-[3-(4-formyl-phenyl)-1-isopropyl-1H-indol-6-yl]-methanesulfonamide and hydroxylamine hydrochloride into a round bottom flask under nitrogen. Add ethanol (10 mL), tetrahydrofuran (10 mL) and pyridine. Warm to 60° C., and stir for 2 hours. Dilute with ethyl acetate (20 mL), and wash with 1N hydrochloric acid. Dry the organic layer over sodium sulfate, and concentrate in vacuo. Purify the residue by flash chromatography on silica (5-40% ethyl acetate in dichloromethane) to give N-{3-[4-(Hydroxyimino-methyl)-phenyl]-1-isopropyl-1H-indol-6-yl}-methanesulfonamide (241.1 mg, 69%). LRMS (API ES+)=372.0 (M+H).

Workup

  1. washwash with 1N hydrochloric acid
  2. dry with materialDry the organic layer over sodium sulfate
  3. concentrationconcentrate in vacuo
  4. customPurify the residue by flash chromatography on silica (5-40% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-05a13021ecc040ef80959690b904df72
Source dataset
uspto-grants-2011_04
Patent number
US07932284B2

Reaction notes

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