4-Toluenesulfonyl chloride → HCID 67377141, compound

HRID 877458Notes

Reaction equation

HRID 877458 reaction equation
[O:1]=[C:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][C:9]([C:15]#[N:16])=[CH:10][CH:11]=3)[C:6]=2[CH2:5][CH2:4][CH2:3]1.[OH-].[K+].[S:19](Cl)([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20]>C1COCC1.O>[O:1]=[C:2]1[C:14]2[N:13]([S:19]([C:22]3[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[C:12]3[C:7](=[CH:8][C:9]([C:15]#[N:16])=[CH:10][CH:11]=3)[C:6]=2[CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 67378120HCID 67378120, compound2×

Product 1

HCID 67377141HCID 67377141, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-oxo-2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile (intermediate 2a) (0.20 g, 0.95 mmol) in THF (2.0 mL), KOH (0.27 g, 4.8 mmol) in water was added followed by TsCl (0.27 g, 1.4 mmol). The reaction mixture was stirred at room temperature for 12 h and then extracted with EtOAc (3×15 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to give the crude compound which was purified by column chromatography [EtOAc-hexane (1:4) as eluant] to obtain the title compound as an off-white solid (0.23 g, 65%). 1H NMR (200 MHz, CDCl3, δ in ppm) 8.0 (d, J=8.4 Hz, 2H), 7.82 (d, J=2.0 Hz, 1H), 7.43 (dd, J=12.0, 2.0 Hz, 1H), 7.39 (d, J=8.4 Hz, 2H), 7.30 (d, J=12.5 Hz, 1H), 2.95 (t, J=9.0 Hz, 2H), 2.66 (t, J=9.0 Hz, 2H), 2.40 (s, 3H), 2.30 (m, 2H).

Workup

  1. extractionextracted with EtOAc (3×15 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto give the crude compound which
  5. customwas purified by column chromatography [EtOAc-hexane (1:4) as eluant]

Sources & evidence

ORD record
ord-5c236bd7379943d1989a2f8dda6fa724
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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