Potassium Carbonate → 2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid pyrrolo[2,3-b]pyridin-1-ylamide

HRID 2382005Notes

Reaction equation

HRID 2382005 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[CH:12][C:11]([C:14](Cl)=[O:15])=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[N:17]1([NH2:26])[C:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:20]2[CH:19]=[CH:18]1.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.O>[N:17]1([NH:26][C:14]([C:11]2[CH:10]=[N:9][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:13][CH:12]=2)=[O:15])[C:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:20]2[CH:19]=[CH:18]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 52239501H-Pyrrolo[2,3-b]pyridin-1-amineHCID 874965532-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid chloride

Product 1

HCID 250993562-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid pyrrolo[2,3-b]pyridin-1-ylamideYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid chloride (1.13 mmol) in EtOAc (20 mL) is added to a stirred solution of pyrrolo[2,3-b]pyridin-1-ylamine (1.13 mmol) and K2CO3 (1.13 mmol) in EtOAc (10 mL) and H2O (20 mL) at rt and the reaction mixture is stirred at rt overnight. EtOAc is evaporated in vacuo, and the resulting solid is collected by filtration to afford 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid pyrrolo[2,3-b]pyridin-1-ylamide (305 mg, 81%) as a solid. MS: 334 (M+H); 1H NMR (300 MHz, CDCl3): δ 6.57 (d, H) 7.13-7.55 (m, 4H), 7.99 (m, H), 8.10-8.40 (m, 3H), 9.27 (s, 2H), 12.57 (br, N—H).

Workup

  1. customEtOAc is evaporated in vacuo
  2. filtrationthe resulting solid is collected by filtration

Sources & evidence

ORD record
ord-82eb4de432ce415ca1be233b23f094b5
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

Loading…