Benzenesulfonyl chloride → 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 2264230Notes

Reaction equation

HRID 2264230 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][N:18]=2)[CH:13]=[CH:12]1.C(N(CC)CC)C>C(Cl)Cl>[C:1]1([S:7]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][N:18]=3)[CH:13]=[CH:12]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 92221H-Pyrrolo(2,3-b)pyridine

Product 1

HCID 8520781-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzenesulfonyl chloride (1b) (98.7 g) was added dropwise into a solution of 7-azaindole (1a) (60.0 g) and triethylamine (56.6 g) in DCM (500 mL) at 0° C. The mixture was warmed to rt and stirred for 2 days to produce a white crystalline product. The white crystals were filtered off and the solution was washed with a saturated aqueous NaHCO3 solution and brine, then dried over MgSO4 and concentrated. The residue was recrystallized in ethyl acetate (200 mL) to provide N-phenylsulfonyl-7-azaindole (1c) (121.31 g, 94%) as white crystals. 1H NMR (400 MHz, CDCl3) δ 8.43 (d, J=4.8 Hz, 1H), 8.18 (d, J=8.0 Hz, 2H), 7.85 (d, J=8.0 Hz, 1H), 7.73 (d, J=4.8 Hz, 1H), 7.57 (t, J=7.6 Hz, 1H), 7.48 (t, J=7.6 HZ, 2H), 7.15 (dd, J=8.0 Hz, 4.8 Hz, 1H), 6.58 (d, J=4.8 Hz, 1H).

Workup

  1. customto produce a white crystalline product
  2. filtrationThe white crystals were filtered off
  3. washthe solution was washed with a saturated aqueous NaHCO3 solution and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was recrystallized in ethyl acetate (200 mL)

Sources & evidence

ORD record
ord-49c2027cdc384a13b877049468f483d1
Source dataset
uspto-grants-2010_12
Patent number
US07855205B2

Reaction notes

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