Potassium Hydroxide → 5-Bromo-2,3-dihydro-pyrrolo[2,3-b]pyridine-1-carboxylic acid amide

HRID 712587Notes

Reaction equation

HRID 712587 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:10][CH2:9][NH:8][C:5]2=[N:6][CH:7]=1.ClC(Cl)(Cl)[C:13]([N:15]=C=O)=[O:14].[OH-].[K+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:10][CH2:9][N:8]([C:13]([NH2:15])=[O:14])[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 76400Trichloroacetyl isocyanateHCID 219640795-Bromo-2,3-dihydro-7-azaindole

Product 1

HCID 1176673865-Bromo-2,3-dihydro-pyrrolo[2,3-b]pyridine-1-carboxylic acid amideYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 5-bromo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine (2.5 g, 12.6 mmol) in DCM (30 mL) is added a trichloroacetyl isocyanate (1.6 mL, 13.2 mmol). After stirring for 1 h at 0° C., a solution of methanolic KOH (1M, 10 mL) is added. The resulting mixture is allowed to warm and stir at room temperature for 16 h. The reaction is concentrated and purified by silica gel column (0-100% EtOAc in heptane) to afford the title compound (2.6 g).

Workup

  1. temperatureto warm
  2. stirringstir at room temperature for 16 h
  3. concentrationThe reaction is concentrated
  4. custompurified by silica gel column (0-100% EtOAc in heptane)

Sources & evidence

ORD record
ord-893c8a81a1f94f1b8c08ac53d2c87b05
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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