Benzenesulfonyl chloride → 3-(1-Benzenesulfonyl-1H-indol-3-yl)-N-(tetrahydro-pyran-2-yloxy)-acrylamide

HRID 84195Notes

Reaction equation

HRID 84195 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[CH:11][C:12]([NH:14][O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)=[O:13])=[CH:2]1.[OH-].[K+].[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[C:24]1([S:30]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([CH:10]=[CH:11][C:12]([NH:14][O:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)=[O:13])=[CH:2]2)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 76528170HCID 76528170, compound

Product 1

HCID 866582683-(1-Benzenesulfonyl-1H-indol-3-yl)-N-(tetrahydro-pyran-2-yloxy)-acrylamideYield 54.1%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 18 (0.52 g, 1.82 mmol), tetrabutylammonium bisulfate (0.09 g, 0.27 mmol) and KOH (0.20 g, 3.63 mmol) in CH2Cl2 (15 mL) was stirred for 20 min, benzenesulfonyl chloride (0.35 ml, 2.72 mmol) was added and stirred at room temperature overnight. The reaction mixture was quenched with water extracted with CH2Cl2 (20 mL×3). The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure to give a yellow residue, which was purified by silica gel chromatography (EtOAc:n-hexane=1:2) to afford 19 (0.42 g)

Workup

  1. stirringstirred at room temperature overnight
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with CH2Cl2 (20 mL×3)
  4. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow residue, which
  7. customwas purified by silica gel chromatography (EtOAc:n-hexane=1:2)

Sources & evidence

ORD record
ord-88f6205fddcf492db24f869888c02aac
Source dataset
uspto-grants-2014_09
Patent number
US08846748B2

Reaction notes

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