Sulfate Ion → 1-(Toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1765589Notes

Reaction equation

HRID 1765589 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.S([O-])([O-])(=O)=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16]([N:1]2[C:9]3=[N:8][CH:7]=[CH:6][CH:5]=[C:4]3[CH:3]=[CH:2]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 1117Sulfate IonHCID 73974-Toluenesulfonyl chlorideHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14798Sodium Hydroxide

Product 1

HCID 14799661-(Toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridineYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 7-azaindole (25 g), para-toluenesulfonyl chloride (44.5 g) and a catalytic amount of tetrabutylammoniun sulfate in dry toluene (300 mL) was added sodium hydroxide (160 g in 500 mL of water). The biphasic solution was stirred at ambient temperature for 3 hours then extracted twice with toluene (100 mL). The combined extracts were dried over magnesium sulfate then concentrated under vacuo. The resultant solid was triturated with diethyl ether then dried at 60° C. under vacuo to yield the title compound (39.74 g) as a pale yellow solid, m.p. 136–138° C.

Workup

  1. extractionthen extracted twice with toluene (100 mL)
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. concentrationthen concentrated under vacuo
  4. customThe resultant solid was triturated with diethyl ether
  5. customthen dried at 60° C. under vacuo

Sources & evidence

ORD record
ord-f432dcf16aa34670b5748aa3fbf1d8e3
Source dataset
uspto-grants-2007_06
Patent number
US07227020B2

Reaction notes

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