4-Formylbenzoic acid → (S)-3,5-dichloro-4-(2-(3,4-dimethoxyphenyl)-2-((4-formylbenzoyl)oxy)ethyl)pyridine 1-oxide

HRID 1529523Notes

Reaction equation

HRID 1529523 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:22])[CH:5]=[C:6]([Cl:21])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)[OH:10].[C:23]([C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=1)(O)=[O:24].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:21][C:6]1[CH:5]=[N+:4]([O-:22])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)[O:10][C:30](=[O:31])[C:29]1[CH:32]=[CH:33][C:26]([CH:23]=[O:24])=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 120884-Formylbenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 71092494(S)-3,5-dichloro-4-(2-(3,4-dimethoxyphenyl)-2-hydroxyethyl)pyridine 1-oxide

Product 1

HCID 86720687(S)-3,5-dichloro-4-(2-(3,4-dimethoxyphenyl)-2-((4-formylbenzoyl)oxy)ethyl)pyridine 1-oxideYield 76%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-3,5-dichloro-4-(2-(3,4-dimethoxyphenyl)-2-hydroxyethyl)-pyridine 1-oxide (0.688 g, 2 mmol), 4-carboxybenzaldehyde (0.300 g, 2 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.767 g, 4 mmol) and 4-(dimethylamino)pyridine (0.122 g, 1 mmol) in anhydrous DCM (30 mL) was stirred at RT for 17 hours. The reaction mixture was partitioned between saturated NaHCO3 (20 mL) and DCM (10 mL) and filtered through a phase separator cartridge. The cartridge was washed thoroughly with DCM and the solvent was removed in vacuo. The crude material was purified by silica gel column chromatography eluting with 2:3 DCM:EtOAc to afford the title compound as a white solid (0.724 g, 76%).

Workup

  1. customThe reaction mixture was partitioned between saturated NaHCO3 (20 mL) and DCM (10 mL)
  2. filtrationfiltered through a phase separator cartridge
  3. washThe cartridge was washed thoroughly with DCM
  4. customthe solvent was removed in vacuo
  5. customThe crude material was purified by silica gel column chromatography
  6. washeluting with 2:3 DCM

Sources & evidence

ORD record
ord-cdfe877e3ece4a7a8b62a55b62d17f80
Source dataset
uspto-grants-2015_07
Patent number
US09090606B2

Reaction notes

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