Potassium Carbonate → HCID 54314594, compound

HRID 1029732Notes

Reaction equation

HRID 1029732 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+].[CH3:28][N:29]=[C:30]=[O:31]>O1CCCC1>[CH3:28][NH:29][C:30](=[O:31])[O:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]([N:12]([CH2:19][CH2:20][CH3:21])[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[CH:3]=[C:2]2[CH3:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 190723493-Methyl-1-[propyl(pyridin-4-yl)amino]-1H-indol-5-ol

Product 1

HCID 54314594HCID 54314594, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution consisting of 3-methyl-1-(propyl-4-pyridinylamino)-1H-indol-5-ol (2.06 g) and tetrahydrofuran (49 ml) was added milled K2CO3 (1.06 g) followed by dropwise addition of methyl isocyanate (0.48 ml) at room temperature under nitrogen. Stirring was continued for 2.3 hours at which time the reaction mixture was filtered through a pad of celite and the solids washed with EtOAc. Concentration afforded the crude product. Purification via flash column chromatography (silica gel, 2% Et3N/EtOAc) afforded 2.30 g of the desired carbamate as an oil. The product was crystallized from ether, m.p. 147°-149° C.

Workup

  1. additionwas added
  2. filtrationthe reaction mixture was filtered through a pad of celite
  3. washthe solids washed with EtOAc
  4. concentrationConcentration
  5. customafforded the crude product
  6. customPurification via flash column chromatography (silica gel, 2% Et3N/EtOAc)

Sources & evidence

ORD record
ord-e269920b89c042c3bb3b39247b94d801
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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