2-propyl-2-(1H-pyrrolo[2,3-b]pyridine-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester → (2-propyl-pyrrolidin-2-yl)-(1H-pyrrolo[2,3-b]pyridin-5-yl)-methanone

HRID 661548Notes

Reaction equation

HRID 661548 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH2:24][CH2:25][CH3:26])[C:13]([C:15]1[CH:16]=[C:17]2[CH:23]=[CH:22][NH:21][C:18]2=[N:19][CH:20]=1)=[O:14])=O)(C)(C)C>Cl>[CH2:24]([C:9]1([C:13]([C:15]2[CH:16]=[C:17]3[CH:23]=[CH:22][NH:21][C:18]3=[N:19][CH:20]=2)=[O:14])[CH2:10][CH2:11][CH2:12][NH:8]1)[CH2:25][CH3:26]

Participants

3

Reactant 1

HCID 666883852-propyl-2-(1H-pyrrolo[2,3-b]pyridine-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58017212(2-propyl-pyrrolidin-2-yl)-(1H-pyrrolo[2,3-b]pyridin-5-yl)-methanoneYield 97%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-propyl-2-(1H-pyrrolo[2,3-b]pyridine-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.240 g, 0.672 mmol) in 1N methanolic HCl (10.1 mL) was stirred at 20° C. under nitrogen for 18 hours. The reaction mixture was concentrated in vacuo then triturated with DCM (5 mL) and concentrated in vacuo to yield (2-propyl-pyrrolidin-2-yl)-(1H-pyrrolo[2,3-b]pyridin-5-yl)-methanone (0.215 g, 0.652 mmol, 97%) as a white powder and as a monohydrochioride salt, MS=258 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthen triturated with DCM (5 mL)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-376e68379c7740af8d9af02ef7e17eec
Source dataset
uspto-grants-2011_12
Patent number
US08084623B2

Reaction notes

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