Ethylenediamine → HCID 25242418, compound

HRID 2367096Notes

Reaction equation

HRID 2367096 reaction equation
[OH:1][C:2]1([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[N:24](COCC[Si](C)(C)C)[CH:23]=[CH:22]3)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O1CCCC1.C(N)CN>[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[OH:1][C:2]1([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][CH:23]=[CH:22]3)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 3

HCID 3301EthylenediamineHCID 8028TetrahydrofuranHCID 67045241HCID 67045241, compound

Product 1

HCID 25242418HCID 25242418, compoundYield 4%

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolventHCID 2724141Tetrabutylammonium FluorideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 3-hydroxy-2-(phenylmethyl)-3-[1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-indol-5-yl]-2,3-dihydro-1H-isoindol-1-one was taken up in 1M tetrabutylammonium fluoride in tetrahydrofuran (6.0 mL, 6.0 mmol), and ethylenediamine (0.22 mL, 3.6 mmol) was added. The solution was heated to 70° C. for 45 min. The reaction mixture was diluted with ethyl acetate and saturated aqueous sodium bicarbonate solution. The layers were separated and the combined organic layers were dried (sodium sulfate), filtered and concentrated in vacuo. Purification was undertaken via HPLC (reverse-phase, acetonitrile/water with 0.1% trifluoroacetic acid), followed by column chromatography (silica gel, 5% methanol/dichloromethane). The resultant yellow solid was taken up in ethyl acetate and washed with 10% aqueous citric acid solution (3×), dried (sodium sulfate), filtered and concentrated in vacuo. Lyophilization gave 0.0045 g (4%) of 3-hydroxy-3-(1H-indol-5-yl)-2-(phenylmethyl)-2,3-dihydro-1H-isoindol-1-one. 1H NMR (400 MHz, d6-DMSO): 8.20 (d, 1H), 7.91 (dt, 2H), 7.84 (dt, 1H), 7.75 (d, 1H), 7.71 (m, 1H), 7.56 (d, 1H), 7.35 (m, 6H), 4.65 (m, 2H); MS (EI) for C23H18N2O2: 354 (MH+).

Workup

  1. customThe layers were separated
  2. dry with materialthe combined organic layers were dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification
  6. washwashed with 10% aqueous citric acid solution (3×)
  7. dry with materialdried (sodium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a362c1081c64ffb8bdd7aa314d56d59
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

Loading…