Potassium Carbonate → HCID 67903146, compound

HRID 1029735Notes

Reaction equation

HRID 1029735 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[N:4]([N:12]([CH2:19][CH2:20][CH3:21])[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:28]([N:35]=[C:36]=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCCC1>[C:29]1([CH2:28][NH:35][C:36](=[O:37])[O:11][C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[N:4]([N:12]([CH2:19][CH2:20][CH3:21])[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH:3]=[C:2]3[CH3:1])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76639Benzyl isocyanateHCID 190723493-Methyl-1-[propyl(pyridin-4-yl)amino]-1H-indol-5-ol

Product 1

HCID 67903146HCID 67903146, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution consisting of 3-methyl-1-(propyl-4-pyridinylamino)-1H-indol-5-ol (1.80 g) and tetrahydrofuran (43 ml) were added with stirring at room temperature milled potassium carbonate (0.93 g) and benzyl isocyanate (0.87 ml). Stirring was continued under nitrogen for 16 hours. The mixture was filtered through a pad of celite and the solids washed with ethyl acetate. Concentration followed by purification via flash column chromatography (silica gel, 2% Et3N/EtOAc) afforded 2.28 g of the desired carbamate. Recrystallization from ether gave a highly crystalline solid, m.p. 149°-151° C.

Workup

  1. additionwere added
  2. stirringStirring
  3. filtrationThe mixture was filtered through a pad of celite
  4. washthe solids washed with ethyl acetate
  5. concentrationConcentration
  6. customfollowed by purification via flash column chromatography (silica gel, 2% Et3N/EtOAc)

Sources & evidence

ORD record
ord-53b89dbbc68f424785d8e3ba896f00c2
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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