Potassium Carbonate → HCID 25099831, compound

HRID 2382019Notes

Reaction equation

HRID 2382019 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([CH3:14])[C:11]([C:15](Cl)=[O:16])=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[F:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([NH2:28])[CH:23]=[CH:22]2.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.O>[F:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([NH:28][C:15]([C:11]1[C:12]([CH3:14])=[N:13][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:9][CH:10]=1)=[O:16])[CH:23]=[CH:22]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 45078690HCID 45078690, compoundHCID 874957952-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid chloride

Product 1

HCID 25099831HCID 25099831, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 2-(3-fluoro-phenyl)-4-methyl-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 (1 mmol) in EtOAc (10 mL) and H2O (20 mL) at rt, then stirred at rt overnight. EtOAc is evaporated in vacuo, and the resulting solid is collected by filtration. The solid is crystallized from EtOAc/heptane to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-fluoro-indol-1-yl)-amide (62 mg, 17%) as a solid. MS: 365 (M+H); 1H NMR (300 MHz, CDCl3): δ 2.82 (s, H), 6.55 (s, H) 6.90-7.41 (m, 4H), 7.49 (m, H), 8.26 (d, 2H), 8.57 (br, H), 8.96 (br, H). IC50=19 nM.

Workup

  1. customEtOAc is evaporated in vacuo
  2. filtrationthe resulting solid is collected by filtration
  3. customThe solid is crystallized from EtOAc/heptane

Sources & evidence

ORD record
ord-a3a3c3f04201441686edef9ba62f2129
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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