Ethylene Glycol → HCID 57559134, compound

HRID 37963Notes

Reaction equation

HRID 37963 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:12]2[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:11]=2[C:10](=[O:20])[CH2:9][N:8]([C:21](=[O:29])[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH:7]=1)=[O:5])[CH3:2].CC1C=CC(S(O)(=O)=O)=CC=1.[CH2:41](O)[CH2:42][OH:43]>C1(C)C=CC=CC=1.C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:12]2[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:11]=2[C:10]2([O:43][CH2:42][CH2:41][O:20]2)[CH2:9][N:8]([C:21](=[O:29])[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 57559126HCID 57559126, compound

Product 1

HCID 57559134HCID 57559134, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(4-fluorobenzoyl)-1-oxo-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid ethyl ester (39 mg, 10.1 mmol) and TsOH (10 mg) and ethylene glycol (0.2 mL) in toluene (10 mL) was heated to reflux overnight under nitrogen. After cooling, the reaction was diluted with DCM. It was then washed with saturated aqueous NaHCO3 and water and dried over MgSO4. Evaporation of solvent gave a crude product, which was purified by column chromatography on silica gel eluted with MeOH-DCM (2:98) to give the title compound (7.5 mg); 1H-NMR (CDCl3): δ 9.68 (1H, s), 8.24 (1H, d), 7.08 (2H, m), 7.57 (1H, s), 7.41 (2H, m), 7.12 (2H, m), 4.77 (2H, m), 4.55 (2H, m), 4.46 (2H, q), 1.46 (3H, t). MS (ES): 437 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight under nitrogen
  3. temperatureAfter cooling
  4. washIt was then washed with saturated aqueous NaHCO3 and water
  5. dry with materialdried over MgSO4
  6. customEvaporation of solvent
  7. customgave a crude product, which
  8. customwas purified by column chromatography on silica gel
  9. washeluted with MeOH-DCM (2:98)

Sources & evidence

ORD record
ord-9f87a4b866514c4382b1c8316a8fedd8
Source dataset
uspto-grants-2013_09
Patent number
US08524704B2

Reaction notes

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