Sodium Iodide → HCID 18671695, compound

HRID 1057627Notes

Reaction equation

HRID 1057627 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[C:10]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:23])[C:5]2=1.Cl.[CH2:25]([N:27]([CH2:31][CH3:32])[CH2:28][CH2:29]Cl)[CH3:26].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[C:10]1[CH:9]=[CH:8][CH:7]=[C:6]([O:23][CH2:26][CH2:25][N:27]([CH2:31][CH3:32])[CH2:28][CH3:29])[C:5]2=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 18671690HCID 18671690, compound

Product 1

HCID 18671695HCID 18671695, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Chloro-9-(4-fluorobenzyl)-9H-carbazol-4-ol (0.0619 g, 0.19 mmol), 2-diethylaminoethylchloride hydrochloride (0.0494 g, 0.29 mmol), potassium carbonate (0.0750 g, 0.54 mmol), sodium iodide (0.0021 g, 0.014 mmol) and DMF (1 mL) are heated at 85° C. for 4 h. After the mixture had cooled, it is partitioned between water and ether. The aqueous layer is also extracted with ethyl acetate several times. The combined organic layers are dried over magnesium sulfate and concentrated to an oil. The oil is chromatographed on silica gel (75 mL) using methanol/dichloromethane (1/99 to 2/98 to 4/96) to give 0.0591 g (73%) of the title compound; mp 99-99.5° C.; MS (ESI+) for C25H26ClFN2O m/z 425.2 (M+H)+; IR (drift) 2972, 1588, 1507, 1467, 1454, 1342, 1270, 1221, 1151, 1123, 817, 799, 778, 740, 714 cm−1; 1H NMR (CDCl3) δ1.15, 2.75, 3.12, 4.33, 5.44, 6.71, 6.93, 7.04, 7.20, 7.34, 8.33. Anal. Calcd for C25H26ClFN2O: C, 70.66; H, 6.17; N, 6.59. Found: C, 70.23; H, 6.05; N, 6.61.

Workup

  1. temperatureAfter the mixture had cooled
  2. customit is partitioned between water and ether
  3. extractionThe aqueous layer is also extracted with ethyl acetate several times
  4. dry with materialThe combined organic layers are dried over magnesium sulfate
  5. concentrationconcentrated to an oil
  6. customThe oil is chromatographed on silica gel (75 mL)

Sources & evidence

ORD record
ord-076a7be8f2ce4c639acb83226afad311
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

Loading…