Benzenesulfonyl chloride → 5-Chloro-1-(phenylsulfonyl)-4-azaindole

HRID 628248Notes

Reaction equation

HRID 628248 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[CH:9][NH:10][C:5]2=[CH:4][CH:3]=1.[C:11]1([S:17](Cl)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[CH:9][N:10]([S:17]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)(=[O:19])=[O:18])[C:5]2=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 123842375-Chloro-1H-pyrrolo(3,2-b)pyridine

Product 1

HCID 181764365-Chloro-1-(phenylsulfonyl)-4-azaindoleYield 90.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 5-chloro-1H-pyrrolo[3,2-b]pyridine (5.0 g, 33 mmol, Adesis) in DCM (42 mL) was added benzenesulfonyl chloride (5.4 mL, 43 mmol, Aldrich), triethylamine (7.3 mL, 52 mmol) and 4-dimethylaminopyridine (0.40 g, 3.3 mmol). After stirring at room temperature for 1 hour, the mixture was diluted with EtOAc, washed with water (2×), brine, dried over sodium sulfate, filtered and concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-20% EtOAc in hexanes to afford product as a white solid (8.7 g, 90%).

Workup

  1. washwashed with water (2×), brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was purified by flash chromatography
  6. washeluting with a gradient from 0-20% EtOAc in hexanes

Sources & evidence

ORD record
ord-624d459d23f84544ae199499a28483cd
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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