Potassium Carbonate → HCID 90416906, compound

HRID 1484815Notes

Reaction equation

HRID 1484815 reaction equation
C([O-])([O-])=O.[K+].[K+].[OH:7][C:8]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:9]=1[CH:10]=[O:11].Cl[CH2:18][C:19]1[CH2:20][CH2:21][N:22]([C:31](=[O:33])[CH3:32])[CH2:23][C:24]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C.CCOC(C)=O>[C:31]([N:22]1[CH2:23][C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:19]([CH2:18][O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:9]=2[CH:10]=[O:11])[CH2:20][CH2:21]1)(=[O:33])[CH3:32]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 102858012,6-DihydroxybenzaldehydeHCID 90417175HCID 90417175, compound

Product 1

HCID 90416906HCID 90416906, compoundYield 34.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of K2CO3 (40 mg, 0.28 mmol) and 2,6-dihydroxybenzaldehyde (40 mg, 0.28 mmol) in DMF (1 mL) was added a solution of 1-(4-(chloromethyl)-5-phenyl-3,6-dihydropyridin-1(2H)-yl)ethan-1-one (35 mg, 0.14 mmol) in DMF (1 mL), the mixture was heated at 50° C. for 3 h, cooled to room temperature, and was diluted with EtOAc, organic layer was separated and aqueous layer was extracted with EtOAc. EtOAc layers were combined, washed with Sat. NaHCO3, brine, dried over Na2SO4, and was concentrated to give crude oil, which was purified by column (DCM/MeOH=90:10) to give 2-((1-acetyl-5-phenyl-1,2,3,6-tetrahydropyridin-4-yl)methoxy)-6-hydroxybenzaldehyde (17 mg). 1H NMR (400 MHz, CDCl3, NMR shows rotamer exist, only one set of signal was reported) □ (ppm) 11.93 (s, 1H), 10.36 (s, 1H), 7.34 (m, 5H), 7.22 (m, 1H), 6.49 (d, J=8.8 Hz, 1H), 6.10 (d, J=8.8 Hz, 1H), 4.47 (s, 2H), 4.32 (s, 2H), 3.68 (t, J=6.0 Hz, 2H), 2.47 (m, 2H), 2.18 (s, 3H); MS (ESI) m/z 352.5 [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. customwas separated
  3. extractionaqueous layer was extracted with EtOAc
  4. washwashed with Sat. NaHCO3, brine
  5. dry with materialdried over Na2SO4
  6. concentrationwas concentrated
  7. customto give crude oil, which
  8. customwas purified by column (DCM/MeOH=90:10)

Sources & evidence

ORD record
ord-016abf629d73436e87b574972ec6bf5a
Source dataset
uspto-grants-2016_08
Patent number
US09422279B2

Reaction notes

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