Potassium Carbonate → HCID 86303714, compound

HRID 1484827Notes

Reaction equation

HRID 1484827 reaction equation
Cl[CH2:2][C:3]1[C:4]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[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:12]1[CH:13]=[CH:14][C:9]([C:4]2[C:3]([CH2:2][O:16][C:17]3[C:18]([CH:25]=[O:26])=[CH:19][C:20]([O:23][CH3:24])=[N:21][CH:22]=3)=[CH:8][CH:7]=[CH:6][N:5]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69106620HCID 69106620, compoundHCID 722124985-Hydroxy-2-methoxyisonicotinaldehyde

Product 1

HCID 86303714HCID 86303714, 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-(4-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, 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 0.05% TFA and MeCN (20.0% MeCN up to 60.0% 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 148.2 mg (20%) of 5-[[2-(4-chlorophenyl)pyridin-3-yl]methoxy]-2-methoxypyridine-4-carbaldehyde; bis(trifluoroacetic acid) as a yellow solid. 1HNMR (300 MHz, DMSO-d6) δ 10.05 (s, 1H), 8.69 (m, 1H), 8.16 (m, 2H), 7.64 (m, 2H), 7.50 (m, 3H), 5.32 (s, 2H), 3.81 (s, 3H); MS (ESI) m/z 355 [M+H]+.

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 0.05% TFA and MeCN (20.0% MeCN up to 60.0% in 10 min
  5. waitup to 95.0% in 2 min
  6. waitdown to 20.0% in 1 min)
  7. customThis resulted in 148.2 mg (20%) of 5-[[2-(4-chlorophenyl)pyridin-3-yl]methoxy]-2-methoxypyridine-4-carbaldehyde

Sources & evidence

ORD record
ord-0db8d56a97fe4e01812b797eaeb45776
Source dataset
uspto-grants-2016_08
Patent number
US09422279B2

Reaction notes

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