Propane sultone → 3-(2,3,3-Trimethyl-3H-pyrrolo[2,3-b]pyridin-7-ium-7-yl)propane-1-sulfonate

HRID 1480506Notes

Reaction equation

HRID 1480506 reaction equation
[CH3:1][C:2]1[C:3]([CH3:12])([CH3:11])[C:4]2[C:5]([N:10]=1)=[N:6][CH:7]=[CH:8][CH:9]=2.[CH2:13]1[CH2:19][S:16](=[O:18])(=[O:17])[O:15][CH2:14]1>C(#N)C.C(OCC)(=O)C>[CH3:1][C:2]1[C:3]([CH3:12])([CH3:11])[C:4]2[C:5]([N:10]=1)=[N+:6]([CH2:14][CH2:13][CH2:19][S:16]([O-:18])(=[O:17])=[O:15])[CH:7]=[CH:8][CH:9]=2

Participants

5

Reactant 2

HCID 14264Propane sultoneHCID 222668362,3,3-Trimethyl-3H-pyrrolo[2,3-b]pyridine

Product 1

HCID 577633353-(2,3,3-Trimethyl-3H-pyrrolo[2,3-b]pyridin-7-ium-7-yl)propane-1-sulfonateYield 138.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 9 g of 2,3,3-trimethyl-3H-pyrrolo[2,3-b]pyridine and 20.6 g of 1,3-propanesultone is heated at 60° C. for 3 h. The reaction mixture is then dissolved in 100 mL of acetonitrile, and 300 mL of ethyl acetate is added. The resulting sticky solid is again stirred in 300 mL of ethyl acetate to yield 22 g of the product.

Sources & evidence

ORD record
ord-ce45c61d17174cffa29acf2c8a28c10b
Source dataset
uspto-grants-2016_08
Patent number
US09408924B2

Reaction notes

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