Pentane → HCID 18671657, compound

HRID 1057625Notes

Reaction equation

HRID 1057625 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH2:7][C:6](=[O:15])[C:5]2=1.CCCCC.[H-].[Na+].[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:28][C:27]1[CH:30]=[CH:31][C:24]([F:23])=[CH:25][CH:26]=1)[C:10]1[CH2:9][CH2:8][CH2:7][C:6](=[O:15])[C:5]2=1

Participants

6

Reactant 4

HCID 8003PentaneHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 3357036-Chloro-4-oxo-1,2,3,4-tetrahydrocarbazole

Product 1

HCID 18671657HCID 18671657, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6-Chloro-1,2,3,9-tetrahydro-4H-carbazol-4-one (0.4042 g, 0.0018 mol) is added to a slurry of pentane-washed NaH (0.091 g, 0.0023 mol) in DMF (2 mL) and after stirring for 20 min, p-fluorobenzyl bromide (0.28 mL, 0.0023 mol) is added. Additional DMF (1 mL) is added and the mixture is stirred for 4 h, at which time the mixture is partitioned between aq. sodium bicarbonate and ethyl acetate. The combined organic layers are washed with water, dried over sodium sulfate and concentrated to dryness. The resulting solids are chromatographed on silica gel (200 mL) using dichloromethane/heptane (60/40 and 80/20) to give 0.5519 g (92%) of the title compound; mp 207-207.75° C.; MS (ESI+) for C19H15ClFNO m/z 328.1 (M+H)+; IR (drift) 1628, 1511, 1467, 1448, 1360, 1226, 1218, 1145, 1096, 878, 849, 840, 804, 764, 649 cm−1; 1H NMR (CDCl3) δ2.23, 2.58, 2.86, 5.27, 6.99, 7.16, 8.27. Anal. Calcd for C19H15ClFNO: C, 69.62; H, 4.61; N, 4.27. Found (av): C, 69.08; H, 4.50; N, 4.26.

Workup

  1. stirringthe mixture is stirred for 4 h, at which time the mixture
  2. customis partitioned between aq. sodium bicarbonate and ethyl acetate
  3. washThe combined organic layers are washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe resulting solids are chromatographed on silica gel (200 mL)

Sources & evidence

ORD record
ord-d4661a97358a466a9c950713888c69d4
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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