Thionyl Chloride → 1-benzenesulfonyl-5-chloromethyl-1H-pyrrolo[2,3-b]pyridine

HRID 1515680Notes

Reaction equation

HRID 1515680 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([CH2:19]O)[CH:18]=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:23])=O>ClCCl>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([CH2:19][Cl:23])[CH:18]=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67229270(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-methanol

Product 1

HCID 672282211-benzenesulfonyl-5-chloromethyl-1H-pyrrolo[2,3-b]pyridineYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-methanol (4.2 g, 14.6 mmol) in dichloromethane (20 mL) at 0° C. was added a solution of thionyl chloride (1.6 mL, 21.9 mmol) in dichloromethane (5 mL) and then stirred for 2 h. The reaction mixture was concentrated in vacuo and the residue was extracted with ethyl acetate, washed with a saturated aqueous sodium bicarbonate solution (2×100 mL), brine, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 1-benzenesulfonyl-5-chloromethyl-1H-pyrrolo[2,3-b]pyridine (3.3 g, 75%) as a light yellow solid which was used in the next step without further purification: LC/MS m/e calcd for C14H11ClN2O2S [M+H]+ 307.77, observed 307.1.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionthe residue was extracted with ethyl acetate
  3. washwashed with a saturated aqueous sodium bicarbonate solution (2×100 mL), brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2af8d72812c9474b923cdcd96e9cdc17
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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