Pentane → HCID 18671659, compound

HRID 1057598Notes

Reaction equation

HRID 1057598 reaction equation
[Cl: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>[Cl: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 hydride2×HCID 680214-Fluorobenzyl bromideHCID 12375583HCID 12375583, compound

Product 1

HCID 18671659HCID 18671659, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

8-Chloro-1,2,3,9-tetrahydro-4H-carbazol-4-one (0.1973 g, 0.90 mmol) is added to a slurry of pentane-washed NaH (0.0286 g, 0.72 mmol) in DMF (1 mL) and, after stirring for 22 min, p-fluorobenzyl bromide (0.14 mL, 0.0011 mol) is added. Starting material remained after 30 min, so additional NaH (0.0166 g, 0.42 mmol) and DMF (1.8 mL) are added. The mixture is stirred for 1 h, at which time the mixture 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 recrystallized from 30% ethyl acetate/hexane and dichloromethane to give 0.2088 g (71%) of the title compound; mp 166-166.5° C.; MS (ESI+) for C19H15ClFNO m/z 328.1 (M+H)+; IR (drift) 1639, 1607, 1510, 1485, 1449, 1426, 1413, 1226, 1189, 1157, 1108, 1095, 830, 790, 734 cm−1; 1H NMR (CDCl3) δ2.22, 2.59, 2.84, 5.78, 6.97, 7.19, 8.27. Anal. Calcd for C19H15ClFNO: C, 69.62; H, 4.61; N, 4.27. Found: C, 69.44; H, 4.55; N, 4.34.

Workup

  1. waitStarting material remained after 30 min
  2. stirringThe mixture is stirred for 1 h, at which time the mixture
  3. customis partitioned between aq. sodium bicarbonate and ethyl acetate
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe resulting solids are recrystallized from 30% ethyl acetate/hexane and dichloromethane

Sources & evidence

ORD record
ord-535f5471f53a4904839ab3c809bb2b68
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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