Pentane → HCID 18671664, compound

HRID 1057619Notes

Reaction equation

HRID 1057619 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:14]=1[NH:13][C:12]1[CH2:11][CH2:10][CH2:9][C:8](=[O:15])[C:7]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>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:14]=1[N:13]([CH2:28][C:27]1[CH:30]=[CH:31][C:24]([F:23])=[CH:25][CH:26]=1)[C:12]1[CH2:11][CH2:10][CH2:9][C:8](=[O:15])[C:7]2=1

Participants

6

Reactant 4

HCID 8003PentaneHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 221477458-Fluoro-1,2,3,9-tetrahydro-4H-carbazol-4-one

Product 1

HCID 18671664HCID 18671664, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Fluoro-1,2,3,9-tetrahydro-4H-carbazol-4-one (0.1416 g, 0.70 mmol) is added to a slurry of pentane-washed NaH (0.0400 g, 0.0010 mol) in DMF (2 mL) and after stirring for 30 min, p-fluorobenzyl bromide (0.11 mL, 0.88 mmol) is added. After the mixture had stirred for 2.3 h, it is partitioned between aq. sodium bicarbonate and ethyl acetate. The organic layer is dried over sodium sulfate and concentrated to dryness. The resulting solids are chromatographed on silica gel (100 mL) using first dichloromethane (100%) and then methanol/dichloromethane (2/98). The product fractions are combined and rechromatographed on silica gel (50 mL) using acetone/heptane/NH4OH (15/85/0.25) and then recrystallized using ethyl acetate/hexane to give 0.0932 g (43%) of the title compound; mp 177-178° C.; MS (ESI−) for C19H15F2NO m/z 310.1 (M−H)−; IR (drift) 1638, 1630, 1509, 1496, 1459, 1436, 1413, 1361, 1249, 1222, 1194, 1158, 1125, 830, 790 cm−1; 1H NMR (CDCl3) δ2.24, 2.58, 2.86, 5.47, 6.89-7.02, 7.16, 8.06. Anal. Calcd for C19H15F2NO: C, 73.30; H, 4.86; N, 4.50. Found: C, 73.40; H, 4.83; N, 4.50.

Workup

  1. stirringAfter the mixture had stirred for 2.3 h
  2. customit is partitioned between aq. sodium bicarbonate and ethyl acetate
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. concentrationconcentrated to dryness
  5. customThe resulting solids are chromatographed on silica gel (100 mL)
  6. customrechromatographed on silica gel (50 mL)
  7. customrecrystallized

Sources & evidence

ORD record
ord-3325018c2a04496e8320926179503474
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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