4-Toluenesulfonyl chloride → 4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine

HRID 506778Notes

Reaction equation

HRID 506778 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[NH:10][CH:11]=[CH:12][C:5]=12.[S:13](Cl)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14]>O.[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O.C1(C)C=CC=CC=1>[Cl:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[N:10]([S:13]([C:16]3[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:11]=[CH:12][C:5]=12

Participants

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 81672684-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridineYield 78.8%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Add NaOH (3.6 g, 90.2 mmol) as solution in H2O (14 mL) to a solution of 4-chloroazaindole 24 (0.84 g, 5.50 mmol), TsCl (1.154 g, 6.053 mmol) and Bu4NHSO4 (16 μL, 50% in H2O) in toluene (16 mL). After stirring the reaction medium for 2.5 h at room temperature, the two-phase reaction medium is then extracted with EtOAc (2×), dried (MgSO4) and concentrated under vacuum. Flash chromatography gives 25 (1.33 g, 78%) as a white solid: 1H NMR (CDCl3) δ 8.28 (d, 1H, J=5.1 Hz), 8.04 (dd, 2H, J=8.5, 2.0 Hz), 7.75 (d, 2H, J=4.0 Hz), 7.26 (d, 1H, J=8.4 Hz), 7.17 (d, 1H, J=5.1 Hz), 6.67 (d, 1H, J=4.2 Hz), 2.37 (s, 3H), TLC (EtOAc at 40%/heptane) Rf=0.50, m/z obs.=307 (M+1), 308.9.

Workup

  1. customthe two-phase reaction medium
  2. extractionis then extracted with EtOAc (2×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8660438397ad447796d3296b430ff677
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

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