Sodium Iodide → HCID 9953072, compound

HRID 1057606Notes

Reaction equation

HRID 1057606 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:20])[C:14]=3[C:13]3[C:8]2=[C:9]([CH3:21])[CH:10]=[CH:11][CH:12]=3)=[CH:4][CH:3]=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>[CH2:25]([N:27]([CH2:31][CH3:32])[CH2:28][CH2:29][O:20][C:15]1[C:14]2[C:13]3[C:8](=[C:9]([CH3:21])[CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:6][C:5]3[CH:22]=[CH:23][C:2]([F:1])=[CH:3][CH:4]=3)[C:19]=2[CH:18]=[CH:17][CH:16]=1)[CH3:26]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 12044737HCID 12044737, compound

Product 1

HCID 9953072HCID 9953072, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9-(4-Fluorobenzyl)-8-methyl-9H-carbazol-4-ol (0.0176 g, 0.058mmol), 2-diethylaminoethylchloride hydrochloride (0.0144 g, 0.084 mmol), potassium carbonate (0.0332 g, 0.24 mmol), sodium iodide (0.0008 g, 0.0053 mmol) and DMF (1 mL) are heated at 85° C. for 4 h. After the mixture had cooled, it is partitioned between water and ethyl acetate. The aqueous layer is also washed with dichloromethane. The combined organic layers are dried over magnesium sulfate and concentrated to an oil. The oil is chromatographed on silica gel (10 mL) using methanol/dichloromethane (1/99 and 2/98) to give 0.0148 g (55%) of the title compound; MS (ESI+) for C26H29FN2O m/z 405.2 (M+H)+; 1H NMR (CDCl3) δ1.23, 2.65, 2.88, 3.26, 4.47, 5.75, 6.73, 6.95, 7.15, 7.33, 8.29. Anal. Calcd for C26H29FN2O: C, 77.20; H, 7.22; N, 6.93. Found: C, 73.47; H, 7.06; N, 6.53.

Workup

  1. temperatureAfter the mixture had cooled
  2. customit is partitioned between water and ethyl acetate
  3. washThe aqueous layer is also washed with dichloromethane
  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 (10 mL)

Sources & evidence

ORD record
ord-7739eca80b4f442f8cfc3df408ca78c2
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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