Thionyl Chloride → 5-chloromethyl-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine

HRID 1515674Notes

Reaction equation

HRID 1515674 reaction equation
[CH:1]1([CH2:6][CH:7]([C:18]2[NH:28][C:21]3=[N:22][CH:23]=[C:24]([CH2:26]O)[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:31])=O>ClCCl>[Cl:31][CH2:26][C:24]1[CH:25]=[C:20]2[CH:19]=[C:18]([CH:7]([C:8]3[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=3)[CH2:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[NH:28][C:21]2=[N:22][CH:23]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 53250433{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-methanol

Product 1

HCID 672294355-chloromethyl-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridineYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of {2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-methanol (prepared as in Example 8, 800 mg, 1.92 mmol) in dichloromethane (20 mL) at 0° C. was added a solution of thionyl chloride (0.36 mL, 4.89 mmol) in dichloromethane (2 mL) and the mixture was stirred for 2 h. The resulting mixture was concentrated in vacuo and the residue was extracted with ethyl acetate, washed with a saturated aqueous sodium bicarbonate solution (2×50 mL), brine, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 5-chloromethyl-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (798 mg, quant.) as a light yellow solid which was used in the next step without further purification: LC/MS m/e calcd for C22H25ClN2O2S [M+H]+ 417.97, observed 417.0.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. extractionthe residue was extracted with ethyl acetate
  3. washwashed with a saturated aqueous sodium bicarbonate solution (2×50 mL), brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-87ad3c57df714b3b9842a01dab120258
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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