Nitrogen → HCID 86666550, compound

HRID 75974Notes

Reaction equation

HRID 75974 reaction equation
N#N.[CH2:3]([O:10][C:11]1[CH:12]=[C:13]([CH:18]=[C:19]([OH:21])[CH:20]=1)[C:14]([O:16][CH3:17])=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].F[C:29]1[CH:36]=[CH:35][C:32]([CH:33]=[O:34])=[CH:31][CH:30]=1>CN(C=O)C.O>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]([CH:18]=[C:19]([O:21][C:29]2[CH:36]=[CH:35][C:32]([CH:33]=[O:34])=[CH:31][CH:30]=2)[CH:20]=1)[C:14]([O:16][CH3:17])=[O:15])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 7472028Methyl 3-(benzyloxy)-5-hydroxybenzoate2×

Product 1

HCID 86666550HCID 86666550, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a single necked round bottomed flask fitted with stop cock with N2(g) balloon, in DMF was added Methyl 3-(benzyloxy)-5-hydroxybenzoate (24 g) (Intermediate 12). Under stirring, potassium carbonate (38 g) followed by 4-fluorobenzaldehyde (13.84 g) were added at room temperature. The reaction was heated at 90° C. for 16 h with constant stirring. The reaction mixture was diluted with water and extracted with EtOAc. All organic layers were combined and washed with water, brine, dried over anhydrous sodium sulphate, filtered and concentrated under vacuum to get crude thick liquid product. The crude product was purified by flash column chromatography to yield title compound (32.5 g).

Workup

  1. additionwere added at room temperature
  2. extractionextracted with EtOAc
  3. washwashed with water, brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto get crude thick liquid product
  8. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-67941696561f4572973b640745d35d6a
Source dataset
uspto-grants-2014_09
Patent number
US08835469B2

Reaction notes

Loading…