Triethylamine → 2-[2-cyclopentyl-1-(4-ethenesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine

HRID 1515818Notes

Reaction equation

HRID 1515818 reaction equation
[CH:1]1([CH2:6][CH:7]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH2:26][CH2:27]O)(=[O:25])=[O:24])=[CH:19][CH:18]=2)[C:8]2[NH:16][C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.CS(Cl)(=O)=O>ClCCl>[CH:1]1([CH2:6][CH:7]([C:8]2[NH:16][C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)[C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH:26]=[CH2:27])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 532521832-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-benzenesulfonyl}-ethanol

Product 1

HCID 672293482-[2-cyclopentyl-1-(4-ethenesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridineYield 66.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (2-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-benzenesulfonyl}-ethanol (prepared as in Example 91, 600 mg, 1.5 mmol) and triethylamine (0.42 ml, 3.0 mmol) in dichloromethane (15 mL) at 0° C. was added a solution of methanesulfonyl chloride (0.18 ml, 2.2 mmol) in dichloromethane. The mixture was stirred at 0° C. for 30 min. The reaction was quenched with a water (20 mL). The mixture was extracted with dichloromethane (2×50 mL), washed with brine (3×20 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 50% ethyl acetate/dichloromethane) afforded 2-[2-cyclopentyl-1-(4-ethenesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (380 mg, 66%) as a solid: LC/MS m/e calcd for C22H24N2O2S [M+H]+ 381.51, observed 381.0.

Workup

  1. customThe reaction was quenched with a water (20 mL)
  2. extractionThe mixture was extracted with dichloromethane (2×50 mL)
  3. washwashed with brine (3×20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 50% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-588cfbececf64f6eb7a30400053d5709
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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