Benzenesulfonyl chloride → HCID 49758931, compound

HRID 1020906Notes

Reaction equation

HRID 1020906 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][N:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl.[OH-].[Na+].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:12]1([S:18]([N:7]2[C:8]3[C:4](=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][N:9]=3)[CH:5]=[CH:6]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 112405674-Methoxy-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 49758931HCID 49758931, compoundYield 73.9%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a mixture of 4-methoxy-7-azaindole (6.4 g, 43.2 mmol) in dichloromethane (200 mL) and 50% aqueous sodium hydroxide (200 mL) was added benzenesulfonyl chloride (6.1 mL, 47.5 mmol) and tetrabutylammonium bromide (1.4 g, 4.3 mmol). The mixture was stirred vigorously at room temperature for 18 hours. The organic phase was washed with water and brine, dried (MgSO4), filtered and concentrated. The crude product was recrystallized from ethyl acetate and hexanes to give 9.2 g of 1-benzenesulfonyl-4-methoxy-7-azaindole as a yellow solid. 1H NMR (DMSO-d6) δ 8.30 (d, J=5 Hz, 1H), 8.18 (d, 1 Hz, 1H), 7.58 (m, 2H), 7.47 (m, 2H), 6.67 (d, 4 Hz, 1H), 6.61 (d, 4 Hz, 1H), 3.94 (s, 3H). MS (m/z) 289 (M+H).

Workup

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was recrystallized from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-5038c587efa045b88c5723d41efc326f
Source dataset
uspto-grants-2014_05
Patent number
US08716493B2

Reaction notes

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