Sodium Iodide → HCID 9823700, compound

HRID 1057600Notes

Reaction equation

HRID 1057600 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:14]=1[N:13]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[C:12]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:23])[C:7]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]=[CH:4][CH:5]=[C:6]2[C:14]=1[N:13]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[C:12]1[CH:11]=[CH:10][CH:9]=[C:8]([O:23][CH2:26][CH2:25][N:27]([CH2:31][CH3:32])[CH2:28][CH3:29])[C:7]2=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 12967330HCID 12967330, compound

Product 1

HCID 9823700HCID 9823700, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Chloro-9-(4-fluorobenzyl)-9H-carbazol-4-ol (0.1038 g, 0.32mmol), 2-diethylaminoethylchloride hydrochloride (0.0831 g, 0.48 mmol), potassium carbonate (0.1248 g, 0.90 mmol), sodium iodide (0.0037 g, 0.025 mmol) and DMF (1 mL) are heated at 85° C. for 5.5 h. After the mixture had cooled, it is partitioned between water and ether. The combined organic layers are dried over magnesium sulfate and concentrated to an oil. The oil is chromatographed on silica gel (50 mL) using methanol/dichloromethane (1/99, 2/98 and 4/96) to give 0.0741 g (55%) of the title compound; mp 104.5-105.5° C.; MS (ESI+) for C25H26ClFN2O m/z 425.1 (M+H)+; IR (drift) 2966, 2932, 1590, 1506, 1455, 1414, 1354, 1334, 1270, 1221, 1157, 1124, 822, 791, 734 cm−1; 1H NMR (CDCl3) δ1.19, 2.82, 3.20, 4.43, 5.95, 6.73, 6.94, 7.04, 7.16, 7.36, 8.30. Anal. Calcd for C25H26ClFN2O: C, 70.66; H, 6.17; N, 6.59; Cl, 8.34. Found: C, 70.30; H, 6.13; N, 6.54.

Workup

  1. temperatureAfter the mixture had cooled
  2. customit is partitioned between water and ether
  3. dry with materialThe combined organic layers are dried over magnesium sulfate
  4. concentrationconcentrated to an oil
  5. customThe oil is chromatographed on silica gel (50 mL)

Sources & evidence

ORD record
ord-da3a2d0b92b845fc888e58f014a75038
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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