Acetic Acid → 6-Bromo-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-2-one

HRID 1618507Notes

Reaction equation

HRID 1618507 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:15]([O-])=O)[C:5]([C:8]([CH3:14])([CH3:13])[C:9](OC)=[O:10])=[N:6][CH:7]=1.C(O)(=O)C>[Fe]>[Br:1][C:2]1[CH:3]=[C:4]2[NH:15][C:9](=[O:10])[C:8]([CH3:14])([CH3:13])[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 672852172-Pyridineacetic acid, 5-bromo-alpha,alpha-dimethyl-3-nitro-, methyl ester

Product 1

HCID 669587906-Bromo-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Conditions

Temperature
100 °C

Procedure

Prepared according to procedure J using methyl 2-(5-bromo-3-nitropyridin-2-yl)-2-methylpropanoate (0.780 g, 2.57 mmol), acetic acid (14.73 mL, 257 mmol) and iron powder (0.719 g, 12.87 mmol) and heating at 100° C. for 2 h. After purification 6-bromo-3,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-2(3H)-one was obtained as a white solid.

Workup

  1. customPrepared
  2. customAfter purification 6-bromo-3,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-2(3H)-one
  3. customwas obtained as a white solid

Sources & evidence

ORD record
ord-e87f604ec1164b59b3319f3a00a54ba3
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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