Potassium Carbonate → HCID 86303719, compound

HRID 1484810Notes

Reaction equation

HRID 1484810 reaction equation
Cl[CH2:2][C:3]1[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2OC)=[N:5][CH:6]=[CH:7][CH:8]=1.[OH:17][C:18]1[C:19]([CH:26]=[O:27])=[CH:20][C:21]([O:24][CH3:25])=[N:22][CH:23]=1.[C:28](=O)([O-])[O-:29].[K+].[K+]>CC#N>[CH3:25][O:24][C:21]1[CH:20]=[C:19]([CH:26]=[O:27])[C:18]([O:17][CH2:2][C:3]2[C:4]([C:9]3[CH:10]=[CH:11][C:12]([O:29][CH3:28])=[CH:13][CH:14]=3)=[N:5][CH:6]=[CH:7][CH:8]=2)=[CH:23][N:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 722124985-Hydroxy-2-methoxyisonicotinaldehydeHCID 90418300HCID 90418300, compound

Product 1

HCID 86303719HCID 86303719, 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-methoxyphenyl)pyridine (234 mg, 1.00 mmol, 1.00 equiv), 5-hydroxy-2-methoxypyridine-4-carbaldehyde (153 mg, 1.00 mmol, 1.00 equiv), and potassium carbonate (278 mg, 2.01 mmol, 2.00 equiv) in CH3CN (20 mL). The resulting solution was stirred for 4 h at 70° C., and then it was concentrated under vacuum. The crude product (300 mg) was purified by Prep-HPLC with the following conditions (Prep-HPLC-010): Column, SunFire Prep C18 OBD Column, 5 um; 19*150 mm; mobile phase, water with 0.1% TFA and MeCN (20.0% MeCN up to 50.0% in 10 min, up to 95.0% in 2 min, down to 20.0% in 1 min); Detector, Waters 2545 UvDector 254 & 220 nm. This resulted in 265.1 mg (46%) of 2-methoxy-5-[[2-(4-methoxyphenyl)pyridin-3-yl]methoxy]pyridine-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 crude product (300 mg) was purified by Prep-HPLC with the following conditions (Prep-HPLC-010)
  4. waitmobile phase, water with 0.1% TFA and MeCN (20.0% MeCN up to 50.0% in 10 min
  5. waitup to 95.0% in 2 min
  6. waitdown to 20.0% in 1 min)
  7. customThis resulted in 265.1 mg (46%) of 2-methoxy-5-[[2-(4-methoxyphenyl)pyridin-3-yl]methoxy]pyridine-4-carbaldehyde

Sources & evidence

ORD record
ord-94daf698fe0442b59eba9ea19c32e0d9
Source dataset
uspto-grants-2016_08
Patent number
US09422279B2

Reaction notes

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