Benzenesulfonyl chloride → 1-(Phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridine

HRID 1821822Notes

Reaction equation

HRID 1821822 reaction equation
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.C([N-]C(C)C)(C)C.[Li+].[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])(O)=O.[Na+]>O1CCCC1.C1COCC1.CCCCCCC>[C:18]1([S:24]([N:1]2[C:5]3=[CH:6][N:7]=[CH:8][CH:9]=[C:4]3[CH:3]=[CH:2]2)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 92196-AzaindoleHCID 516892Sodium BicarbonateHCID 2724682Lithium diisopropylamide

Product 1

HCID 595812711-(Phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridineYield 80%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21263495Tetrahydrofuran heptaneSolvent

Procedure

To a suspension of 1H-pyrrolo[2,3-c]pyridine (700 mg, 5.9 mmol) in tetrahydrofuran (14.0 mL) was added lithium diisopropylamide (2.9 mL of a 2 M solution in THF/heptane, 5.9 mmol) at −78° C. After 0.5 h, benzenesulfonyl chloride (0.79 mL, 6.2 mmol) was added dropwise. The mixture was allowed to slowly warm to ambient temperature overnight. The reaction mixture was poured into 2% aq NaHCO3 (30 mL) and extracted with EtOAc (2×25 mL). The combined extracts were washed with H2O (20 mL) and saturated NaCl (20 mL), dried (Na2SO4) and concentrated under reduced pressure. Purification by column chromatography (silica gel, 1:1 hexanes/EtOAc) gave 1-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridine (1.2 g, 80%): 1H NMR (500 MHz, DMSO-d6) δ 6.94 (1H, d, J=6.0 Hz), 7.59-7.66 (3H, m), 7.70-7.75 (1H, m), 8.07-8.10 (3H, m), 8.38 (1H, d, J=8.8 Hz), 9.23 (1H, s); ESI MS m/z 259 [C13H10N2O2S+H]+.

Workup

  1. extractionextracted with EtOAc (2×25 mL)
  2. washThe combined extracts were washed with H2O (20 mL) and saturated NaCl (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by column chromatography (silica gel, 1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-ed65318d064e4534a97e01c170c2c4ce
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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