4-Toluenesulfonyl chloride → HCID 19078399, compound

HRID 964759Notes

Reaction equation

HRID 964759 reaction equation
[C:1]1(=[O:30])[N:5]([CH2:6][CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][S:18]([C:21]([F:24])([F:23])[F:22])(=[O:20])=[O:19])[CH:15]=3)[NH:10][CH:9]=2)[C:4](=[O:25])[C:3]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:2]12.[H-].[Na+].[C:33]1([CH3:43])[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=1>C(#N)C>[C:4]1(=[O:25])[N:5]([CH2:6][CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][S:18]([C:21]([F:24])([F:22])[F:23])(=[O:20])=[O:19])[CH:15]=3)[N:10]([S:39]([C:36]3[CH:37]=[CH:38][C:33]([CH3:43])=[CH:34][CH:35]=3)(=[O:41])=[O:40])[CH:9]=2)[C:1](=[O:30])[C:2]2=[CH:29][CH:28]=[CH:27][CH:26]=[C:3]12

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 10503156HCID 10503156, compound

Product 1

HCID 19078399HCID 19078399, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(2-phthalimidoethyl)-5-trifluoromethanesulfonyloxy-1H-indole (Example 10) (0.640 g, 1.46 mmol) in anhydrous acetonitrile (15 mL) was added sodium hydride (60% dispersion in mineral oil, 0.335 g, 23.3 mmol) and the resulting mixture was stirred at room temperature under argon for 5 minutes. p-Toluenesulfonyl chloride (0.333 g, 1.75 mmol) was then added and the mixture stirred at room temperature for 2 hours. After quenching with water (20 mL), the mixture was extracted with ethyl acetate (2×20 mL) and the organic phase dried over magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed on silica gel using hexane/ethyl acetate (4:1 and 2:1) to provide the title compound (0.520 g, 60%) as a white solid. 1H NMR (CDCl3, 300 MHz) δ: 8.03 (d, J=9.0 Hz, 1H), 7.86-7.83 (A2 of A2B2 system, 2H), 7.75-7.72 (B2 of A2B2 system and A2' of A2'B2' system, 4H), 7.58 (s, 1H), 7.51 (d, J=2.4 Hz, 1H), 7.26-7.21 (B2' of A2'B2' system, 2H), 7.20 (dd, J=2.4 and 9.0 Hz, 1H), 3.97 (t, J=7.3 Hz, 2H), 3.05 (t, J-7.3 Hz, 2H), 2.36 (s, 3H).

Workup

  1. stirringthe mixture stirred at room temperature for 2 hours
  2. customAfter quenching with water (20 mL)
  3. extractionthe mixture was extracted with ethyl acetate (2×20 mL)
  4. dry with materialthe organic phase dried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-36a2ec3733074739a6f1ef57e201c26f
Source dataset
uspto-grants-1998_06
Patent number
US05770742

Reaction notes

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