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Sodium Iodide → HCID 9953273, compound

HRID 1057621
Notes
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Reaction equation

HRID 1057621 reaction equation
[F: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>[CH2:25]([N:27]([CH2:31][CH3:32])[CH2:28][CH2:29][O:23][C:8]1[C:7]2[C:6]3[C:14](=[C:2]([F:1])[CH:3]=[CH:4][CH:5]=3)[N:13]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:12]=2[CH:11]=[CH:10][CH:9]=1)[CH3:26]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 18671689HCID 18671689, compound

Product 1

HCID 9953273HCID 9953273, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

8-Fluoro-9-(4-fluorobenzyl)-9H-carbazol-4-ol (0.0226 g, 0.073 mmol), 2-diethylaminoethylchloride hydrochloride (0.0202 g, 0.12 mmol), potassium carbonate (0.0330 g, 0.24 mmol), sodium iodide (0.0018 g, 0.012 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 (2/98 and 4/96) to give 0.0222 g (74%) of the title compound; mp 59-60° C.; MS (ESI+) for C25H27F2N2O m/z 409.3 (M+H)+; 1H NMR (CDCl3) δ1.21, 2.87, 3.22, 4.45, 5.67, 6.74, 6.94, 7.02, 7.14, 7.39, 8.11. Anal. Calcd for C25H26F2N2O: C, 73.51; H, 6.41; N, 6.86. Found: C, 73.05; H, 6.61; N, 6.83.

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-ca411eeea855499193a14009d7f51832
Source dataset
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06514968B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes