Pyridine → HCID 58955091, compound

HRID 1990972Notes

Reaction equation

HRID 1990972 reaction equation
[C:1]1([S:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:19][CH2:20][OH:21])[CH:17]=3)[NH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22]1(C)[C:23]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:25]=[CH:26][CH:27]=1.N1C=CC=C[CH:34]=1>>[CH3:34][C:26]1[CH:27]=[CH:22][C:23]([S:28]([O:21][CH2:20][CH2:19][C:16]2[CH:17]=[C:18]3[C:13](=[CH:14][CH:15]=2)[NH:12][CH:11]=[C:10]3[S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:8])=[O:9])(=[O:29])=[O:30])=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 8623o-Toluenesulfonyl chlorideHCID 58955092HCID 58955092, compound

Product 1

HCID 58955091HCID 58955091, compoundYield 95%

Procedure

To a solution of 2-[3-(phenylsulfonyl)-1H-indol-5-yl]ethanol (0.88 g, 2.91 mmol) in anhydrous pyridine (15 mL) at 0° C. was added toluenesulfonyl chloride (0.58 g, 3.05 mmol). The solution was stirred for 12 hours at room temperature. The mixture was partitioned between ethyl acetate and H2O, and the aqueous layer was extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with 2 M HCl, (2×25 mL), brine, dried (MgSO4), filtered and concentrated under reduced pressure. Silica gel chromatography (50% ethyl acetate/dichloromethane) gave the title compound as a white solid (1.3 g, 95%). Mp: 60-63° C. MS (ES−): 454 (M−H).

Workup

  1. customThe mixture was partitioned between ethyl acetate and H2O
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×30 mL)
  3. washThe combined organic layers were washed with 2 M HCl, (2×25 mL), brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0b6863985dd74b288d5312ac38575100
Source dataset
uspto-grants-2010_01
Patent number
US07645752B2

Reaction notes

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