Sodium Iodide → HCID 9801366, compound

HRID 1057642Notes

Reaction equation

HRID 1057642 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=[CH:9][CH:10]=[C:11]([CH3:21])[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](=[CH:9][CH:10]=[C:11]([CH3:21])[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 18671681HCID 18671681, compound

Product 1

HCID 9801366HCID 9801366, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9-(4-Fluorobenzyl)-6-methyl-9H-carbazol-4-ol (0.0505 g, 0.17 mmol), 2-diethylaminoethylchloride hydrochloride (0.0411 g, 0.24 mmol), potassium carbonate (0.1018 g, 0.74 mmol), sodium iodide (0.0046 g, 0.031 mmol) and DMF (3 mL) are heated at 85° C. for 3 h. After the mixture had cooled, it is partitioned between water and ethyl acetate. The combined organic layers are dried over magnesium sulfate and concentrated to dryness. The residue is chromatographed on silica gel (60 mL) using methanol/dichloromethane (1/99 to 2/98 to 4/96) to give 0.0332 g (50%) of the title compound; MS (ESI+) for C26H29FN2O m/z 405.3 (M+H)+; IR (drift) 2966, 1601, 1506, 1460, 1339, 1269, 1242, 1218, 1150, 1127, 1054, 790, 781, 746, 717 cm−; 1H NMR (CDCl3) δ1.90, 2.55, 2.80, 3.18, 4.39, 5.46, 6.71, 6.94, 7.07, 7.22, 7.33, 8.19. Anal. Calcd for C26H29FN2O: C, 77.20; H, 7.22; N, 6.93. Found: C, 75.79; H, 7.61; N, 6.55.

Workup

  1. temperatureAfter the mixture had cooled
  2. customit is partitioned between water and ethyl acetate
  3. dry with materialThe combined organic layers are dried over magnesium sulfate
  4. concentrationconcentrated to dryness
  5. customThe residue is chromatographed on silica gel (60 mL)

Sources & evidence

ORD record
ord-3abb83ad33be40a8b9474d66e184143c
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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