Potassium Carbonate → HCID 66672889, compound

HRID 422210Notes

Reaction equation

HRID 422210 reaction equation
[C:1]([NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:18])[CH:15]=2)[CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl[C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH2:26])=[O:25])=[CH:22][N:21]=1.C([O-])([O-])=O.[K+].[K+].CC(N(C)C)=O>C1(C)C=CC=CC=1>[C:4]([O:3][C:1](=[O:2])[NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:18][C:20]3[CH:28]=[CH:27][C:23]([C:24](=[O:25])[NH2:26])=[CH:22][N:21]=3)[CH:15]=2)[CH2:10]1)([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 804566-ChloronicotinamideHCID 22719625HCID 22719625, compound

Product 1

HCID 66672889HCID 66672889, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Combine N-Boc-5-hydroxy-2-aminoindane (2.50 g, 10.0 mmol), 6-chloronicotinamide (1.49 g, 9.55 mmol K2CO3 (1.90 g, 14.3 mmol), DMA (25 ml) and toluene (20 ml) in a round bottom flask, equipped with Dean-Stark trap, condenser, and nitrogen inlet. Reflux the suspension for two hours before cooling to ambient temperature. Remove the solids via filtration, wash solids with EtOAc, and concentrate the filtrate/wash on a rotary evaporator. Dissolve the remaining oil in EtOAc, wash with water (2×) and brine, dry (MgSO4) and concentrate. Purify the material on silica gel (20% THF/DCM) to give [5-(5-carbamoyl-pyridin-2-yloxy)-indan-2-yl]carbamic acid tert-butyl ester (870 mg) as a light yellow solid.

Workup

  1. temperatureReflux the suspension for two hours
  2. customRemove the solids
  3. filtrationvia filtration
  4. washwash solids with EtOAc
  5. concentrationconcentrate the
  6. washfiltrate/wash on a rotary evaporator
  7. dissolutionDissolve the remaining oil in EtOAc
  8. washwash with water (2×) and brine
  9. dry with materialdry (MgSO4)
  10. concentrationconcentrate
  11. customPurify the material on silica gel (20% THF/DCM)

Sources & evidence

ORD record
ord-f6113a6855bf4ed8a401daef053be75b
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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