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

HRID 549039Notes

Reaction equation

HRID 549039 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-4eedc4b76f4e4d8590784b50d364a0ae
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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