Sodium Iodide → HCID 9952350, compound

HRID 1057611Notes

Reaction equation

HRID 1057611 reaction equation
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:21])[C:15]=2[C:14]2[C:9]1=[C:10]([F:22])[CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:24]([N:26]([CH2:30][CH3:31])[CH2:27][CH2:28]Cl)[CH3:25].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:25][CH2:24][N:26]([CH2:30][CH3:31])[CH2:27][CH3:28])[C:15]=2[C:14]2[C:9]1=[C:10]([F:22])[CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 18671697HCID 18671697, compound

Product 1

HCID 9952350HCID 9952350, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9-Benzyl-8-fluoro-9H-carbazol-4-ol (0.0273 g, 0.0940 mmol), 2-diethylaminoethylchloride hydrochloride (0.0237 g, 0.14 mmol), potassium carbonate (0.0396 g, 0.29 mmol), sodium iodide (0.0013 g, 0.0087 mmol) and DMF (1 mL) are heated at 80° C. for 3 h. After the mixture had cooled, it is partitioned between water and ethyl acetate. The organic layer is dried over magnesium sulfate and concentrated to an oil. The oil is chromatographed on silica gel (20 mL) using methanol/dichloromethane (1/99 to 2/98 to 3/97) to give 0.0206 g (56%) of the title compound; mp 60-60.5° C.; MS (ESI+) for C25H27FN2O m/z 391.3 (M+H)+; 1H NMR (CDCl3) δ1.17, 2.79, 3.17, 4.39, 5.53, 6.73, 7.02, 7.13, 7.25, 7.38, 8.15. Anal. Calcd for C25H27FN2O: C, 76.89; H, 6.97; N, 7.17. Found: C, 76.33; H, 7.18; N, 7.13.

Workup

  1. temperatureAfter the mixture had cooled
  2. customit is partitioned between water and ethyl acetate
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. concentrationconcentrated to an oil
  5. customThe oil is chromatographed on silica gel (20 mL)

Sources & evidence

ORD record
ord-efb136dfe3c8453eabc8c0624c65dafd
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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