Potassium Carbonate → HCID 25099834, compound

HRID 2382012Notes

Reaction equation

HRID 2382012 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:12]=[CH:11][C:10]([C:13](Cl)=[O:14])=[CH:9][N:8]=1.[F:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([NH2:26])[CH:21]=[CH:20]2.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.O>[F:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([NH:26][C:13]([C:10]1[CH:9]=[N:8][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[N:12][CH:11]=1)=[O:14])[CH:21]=[CH:20]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 450786905-Fluoro-1H-indol-1-amineHCID 86639367HCID 86639367, compound

Product 1

HCID 25099834HCID 25099834, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 2-pyridin-2-yl-pyrimidine-5-carboxylic acid chloride (1 mmol) in EtOAc (20 mL) is added to a stirred solution of 5-fluoro-indol-1-ylamine (1 mmol) and K2CO3 (2 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. The solid is purified by silica gel chromatography eluting with 0-10% MeOH in DCM to afford 2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-indol-1-yl)-amide (65 mg, 20%) as a solid. MS: 334 (M+H); 1H NMR (300 MHz, CD3OD): δ 6.56 (m, H) 7.04 (m, H), 7.28-7.79 (m, 3H), 8.04 (m, H), 8.49 (m, H), 8.81 (m, H), 9.48 (s, 2H), 12.22 (s, N—H). IC50=18 nM.

Workup

  1. customEtOAc is evaporated in vacuo
  2. filtrationthe resulting solid is collected by filtration
  3. customThe solid is purified by silica gel chromatography
  4. washeluting with 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-ffa12310a7f8499c8ee321e4a9e15876
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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