Potassium Carbonate → HCID 86691612, compound

HRID 522614Notes

Reaction equation

HRID 522614 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([N:6]2[C:14](=[O:15])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]2=[O:16])=[N:2]1.Cl[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[N:20]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(Cl)Cl>[F:25][C:21]1[N:20]=[C:19]([CH2:18][N:1]2[CH:5]=[CH:4][C:3]([N:6]3[C:14](=[O:15])[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:7]3=[O:16])=[N:2]2)[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 224820332-(Chloromethyl)-6-fluoropyridine2×HCID 178514958HCID 178514958, compound

Product 1

HCID 86691612HCID 86691612, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of Intermediate 44 (200 mg, 0.938 mmol), 2-(chloromethyl)-6-fluoropyridine (ALLICHEM, 137 mg, 0.938 mmol) and potassium carbonate (ALDRICH, 157 mg, 0.938 mmol) dissolved in acetonitrile (10 mL) was stirred at 80° C. for 6 h. 0.2 eq. of 2-(chloromethyl)-6-fluoropyridine (ALLICHEM, 27.3 mg, 0.188 mmol) and 5 mL of dry acetonitrile were added. Reaction was stirred at 80° C. overnight. Reaction was diluted with DCM and filtered. Solvent was evaporated to dryness. Residue was purified by silica column chromatography using a linear gradient of hexane/EtOAc to yield the title compound (94 mg, 0.292 mmol, 31% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm: 8.02-7.88 (m, 6H), 7.11 (m, 2H), 6.43 (d, 1H), 5.45 (s, 2H). [ES+MS] m/z 323 (MH+).

Workup

  1. customReaction
  2. stirringwas stirred at 80° C. overnight
  3. customReaction
  4. filtrationfiltered
  5. customSolvent was evaporated to dryness
  6. customResidue was purified by silica column chromatography

Sources & evidence

ORD record
ord-422b3eb6a4d6479483d0af96a4add736
Source dataset
uspto-grants-2016_05
Patent number
US09334265B2

Reaction notes

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