Acetic Acid → Indole

HRID 641871Notes

Reaction equation

HRID 641871 reaction equation
CC(=O)CCC(=O)C.CN1CC=C([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22](N)[CH:23]=3)[N:18](S(C3C=CC=CC=3)(=O)=O)[CH:17]=2)CC1.C(O)(=O)C>C(O)C>[NH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=[CH:17]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 80352,5-HexanedioneHCID 59259293HCID 59259293, compound

Product 1

HCID 798Indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hexane-2,5-dione (2 mL) was added to a solution of 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1-(phenylsulfonyl)-1H-indol-5-amine (300 mg, 0.82 mmol) in ethanol (50 mL). Acetic acid (2 mL) was added, and the resulting solution was stirred at room temperature overnight. The solvent was concentrated, followed by column chromatography purification using a 1:10 methanol/dichloromethane solvent system provided 30 mg (8%) of 5-(2,5-dimethyl-1H-pyrrol-1-yl)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1-phenylsulfonyl)-1H-indole as a yellow solid. 1H NMR (CDCl3) δ 8.05 (d, 1H), 7.95 (d, 2H), 7.62 (s, 1H), 7.50 (d, 2H), 7.26 (2H), 6.84 (d, 2H), 6.11 (s, 1H), 5.90 (s, 2H), 3.46 (d, 2H), 3.07 (t, 2H), 2.74 (s, 2H), 2.62 (s, 2H), 1.98 (s, 6H). LC/MS (EI) tR 2.46, m/z 446.0 (M++1)

Workup

  1. concentrationThe solvent was concentrated
  2. customfollowed by column chromatography purification

Sources & evidence

ORD record
ord-8b11d06efe8b4134ad7a4009cfafdd59
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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