Potassium Carbonate → HCID 10245416, compound

HRID 1609850Notes

Reaction equation

HRID 1609850 reaction equation
[Cl:1][C:2]1[C:3]([CH2:10]Cl)=[N:4][CH:5]=[C:6]([O:8][CH3:9])[N:7]=1.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[NH:20][CH:21]=[CH:22][N:23]=2)[N:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:3]([CH2:10][N:23]2[CH:22]=[CH:21][N:20]=[C:19]2[C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([F:12])[N:14]=2)=[N:4][CH:5]=[C:6]([O:8][CH3:9])[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 219192862-Fluoro-6-(1h-imidazol-2-yl)pyridineHCID 222603773-Chloro-2-chloromethyl-5-methoxy-pyrazine

Product 1

HCID 10245416HCID 10245416, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 3-chloro-2-chloromethyl-5-methoxy-pyrazine (350 mg, 1.81 mmol), 2-fluoro-6-(1H-imidazol-2-yl)-pyridine (266 mg, 1.63 mmol) and K2CO3 (750 mg, 5.43 mmol) in DMF (10 mL) is stirred at 45° C. for 16 hours. On cooling, the reaction is quenched with saturated NH4Cl (3 mL) and extracted with DCM (3×20 mL). The combined organic layers are dried and solvent removed. PTLC (silica gel) separation (10% MeOH in DCM) gives 370 mg of 3-chloro-2-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-methoxy-pyrazine as an oil. 1H NMR (CDCl3) 8.08–8.14 (m, 1H), 7.98(s, 1H), 7.81 (dd, 1H), 7.20 (s, 1H), 7.07 (s, 1H), 6.80 (dd, 1H), 6.02 (s, 2H), 3.98 (s, 3H) F. Synthesis of 2-[2-(6-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-methoxy-3-pyridin-2-yl-pyrazine (Compound 7)

Workup

  1. temperatureOn cooling
  2. customthe reaction is quenched with saturated NH4Cl (3 mL)
  3. extractionextracted with DCM (3×20 mL)
  4. customThe combined organic layers are dried
  5. customsolvent removed
  6. customPTLC (silica gel) separation (10% MeOH in DCM)

Sources & evidence

ORD record
ord-2580b6d8a71b4b11bdc6defea9541f1e
Source dataset
uspto-grants-2006_01
Patent number
US06982268B2

Reaction notes

Loading…