Potassium Carbonate → HCID 59750648, compound

HRID 422224Notes

Reaction equation

HRID 422224 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-f0b18c68127a4e8fa1cefd930ad6c118
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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