Potassium Carbonate → HCID 86303867, compound

HRID 1484813Notes

Reaction equation

HRID 1484813 reaction equation
Cl[CH2:2][C:3]1[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])=[N:5][CH:6]=[CH:7][CH:8]=1.[OH:16][C:17]1[C:18]([CH:25]=[O:26])=[CH:19][C:20]([O:23][CH3:24])=[N:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CC#N>[Cl:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:4]1[C:3]([CH2:2][O:16][C:17]2[C:18]([CH:25]=[O:26])=[CH:19][C:20]([O:23][CH3:24])=[N:21][CH:22]=2)=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 722124985-Hydroxy-2-methoxyisonicotinaldehydeHCID 90417196HCID 90417196, compound

Product 1

HCID 86303867HCID 86303867, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Into a 50-mL round-bottom flask, was placed a solution of 3-(chloromethyl)-2-(2-chlorophenyl)pyridine (309 mg, 1.30 mmol, 1.00 equiv), 5-hydroxy-2-methoxypyridine-4-carbaldehyde (200 mg, 1.31 mmol, 1.00 equiv), and potassium carbonate (361 mg, 2.61 mmol, 1.50 equiv) in CH3CN. (20 mL). The resulting solution was stirred for 4 h at 70° C., and then it was concentrated under vacuum. The residue was purified by prep-HPLC. This resulted in 86.2 mg (11%) of 5-[[2-(2-chlorophenyl)pyridin-3-yl]methoxy]-2-methoxypyridine-4-carbaldehyde; bis(trifluoroacetic acid) as a brown oil.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationit was concentrated under vacuum
  3. customThe residue was purified by prep-HPLC
  4. customThis resulted in 86.2 mg (11%) of 5-[[2-(2-chlorophenyl)pyridin-3-yl]methoxy]-2-methoxypyridine-4-carbaldehyde

Sources & evidence

ORD record
ord-308296f312914a7e9c0e5f828ff0c97d
Source dataset
uspto-grants-2016_08
Patent number
US09422279B2

Reaction notes

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