Potassium Carbonate → HCID 59750648, compound

HRID 747974Notes

Reaction equation

HRID 747974 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:12])[CH:9]=2)[CH2:4]1.C([O-])([O-])=O.[K+].[K+].Cl[C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH2:26])=[O:25])=[CH:22][N:21]=1>C1(C)C=CC=CC=1.CC(N(C)C)=O>[OH:1][CH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:12][C:20]3[CH:28]=[CH:27][C:23]([C:24]([NH2:26])=[O:25])=[CH:22][N:21]=3)[CH:9]=2)[CH2:4]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 804566-ChloronicotinamideHCID 59750636HCID 59750636, compound

Product 1

HCID 59750648HCID 59750648, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 31374DimethylacetamideSolvent

Procedure

Combine in a round bottom flask equipped with a stir, Dean Stark Trap filled with toluene, and reflux condenser 2-Hydroxymethyl-indan-5-ol (630.2 mg, 3.84 mmol), K2CO3 (690.0 mg, 5.0 mmol), 6-Chloronicotinamide (600.0 mg, 3.84 mmol) and a solution of DMA:Toluene (15:5 mL). After the reaction refluxes under nitrogen atmosphere for 5 hours, concentrate under reduced pressure and then add ethyl acetate. Wash the organic layer several times with water, then brine, and dry over Na2SO4. After concentrating the reaction mixture under reduced pressure, flash chromatograph using 20% THF, 7% 1N NH3-MeOH, 73% DCM eluent to afforded 481.1 mg, 1.69 mmol (44% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 1.8-2.2 (4H, m), 2.6-2.8 (3H, m), 3.6-3.8 (2H, br d), 3.9-4.0 (1H, m), 6.1-6.6 (2H, br d), 6.8-7.0 (3H, m), 7.2-7.3 (1H, m), 8.1-8.2 (1H, m), 8.6 (1H, s); MS m/z 285 (M+1).

Workup

  1. customCombine in a round bottom flask equipped with a stir, Dean Stark Trap
  2. concentrationconcentrate under reduced pressure
  3. washWash the organic layer several times with water
  4. dry with materialbrine, and dry over Na2SO4
  5. concentrationAfter concentrating the reaction mixture under reduced pressure, flash chromatograph

Sources & evidence

ORD record
ord-bf5b73a001ff4a459847c1f218457a6c
Source dataset
uspto-grants-2008_07
Patent number
US07399774B2

Reaction notes

Loading…