Sodium Iodide → HCID 56597937, compound

HRID 1750067Notes

Reaction equation

HRID 1750067 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][C:12](=[O:16])[NH:13]2)=[CH:8][CH:7]=1.[Na+].[I-].Cl.[Cl:20][C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[N:28]1[CH2:34][CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C([O-])([O-])=O.[K+].[K+]>CC#N>[Cl:20][C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[N:28]1[CH2:34][CH2:33][CH2:32][N:31]([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:15]=[C:14]3[C:9]([CH2:10][CH2:11][C:12](=[O:16])[NH:13]3)=[CH:8][CH:7]=2)[CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 299270147-(3-Bromopropoxy)-3,4-dihydroquinolin-2(1H)-oneHCID 66634061HCID 66634061, compound

Product 1

HCID 56597937HCID 56597937, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of intermediate 3 (142 mg, 0.5 mmol) and NaI (150 mg, 1.0 mmol) in CH3CN was heated to reflux for 30 min and then cooled to rt. Intermediate 2 (196 mg, 0.7 mmol) and anhydrous K2CO3 (173 mg, 1.25 mmol) were added to the mixture. The resulting mixture was heated to reflux for 4 h. Precipitated crystals were filtered off and the filtrate was evaporated under reduced pressure. The residue was extracted with EtOAc. The combined EtOAc layers were washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with DCM/MeOH=30:1) to give 7-(3-(4-(2,3-dichlorophenyl)-1,4-diazepan-1-yl)propoxy)-3,4-dihydroquinolin-2(1H)-one (compound 1) (140 mg, 63%). 1H NMR (300 MHz, CDCl3): δ 8.16 (s, 1H), 7.10-6.98 (m, 4H), 6.53 (dd, J=8.1 Hz, 2.4 Hz, 1H), 6.34 (d, J=2.1 Hz, 1H), 4.01 (t, J=6.6 Hz, 2H), 3.32-3.28 (m, 4H), 2.92-2.87 (m, 6H), 2.76 (t, J=6.6 Hz, 2H), 2.62 (t, J=6.6 Hz, 2H), 2.04-1.97 (m, 4H). HPLC: 99%, RT 2.421 min. MS (ESI) m/z 448.1 [M+H]+. mp: 130-131° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 30 min
  3. temperatureThe resulting mixture was heated
  4. temperatureto reflux for 4 h
  5. customPrecipitated crystals
  6. filtrationwere filtered off
  7. customthe filtrate was evaporated under reduced pressure
  8. extractionThe residue was extracted with EtOAc
  9. washThe combined EtOAc layers were washed with brine
  10. dry with materialdried over anhydrous Na2SO4
  11. concentrationconcentrated in vacuo
  12. custompurified by flash chromatography on silica gel column (elution with DCM/MeOH=30:1)

Sources & evidence

ORD record
ord-9dac372729b04906a62aec387a9d65e2
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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