Potassium Carbonate → HCID 67618203, compound

HRID 1029738Notes

Reaction equation

HRID 1029738 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][CH2:10][NH:11][N:12]1[C:20]2[C:15](=[CH:16][C:17]([OH:21])=[CH:18][CH:19]=2)[C:14]([CH3:22])=[CH:13]1.C([O-])([O-])=O.[K+].[K+].[CH3:29][N:30]=[C:31]=[O:32]>O1CCCC1>[CH3:29][NH:30][C:31](=[O:32])[O:21][C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[N:12]([NH:11][CH2:10][CH2:9][CH2:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[F:1])[CH:13]=[C:14]2[CH3:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 70146441HCID 70146441, compound

Product 1

HCID 67618203HCID 67618203, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution consisting of 1-[(3-fluoro-4-pyridinyl)propylamino]-3-methyl-1H-indol-5-ol (2.10 g) and tetrahydrofuran (47 ml) was added milled K2CO3 (1.02 g) followed by dropwise addition of methyl isocyanate (0.46 ml) at room temperature under nitrogen. Stirring was continued for 15 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, 50% EtOAc/dichloromethane) afforded 2.35 g of the desired carbamate as a solid. The product was recrystallized from ether, m.p. 163°-164° 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, 50% EtOAc/dichloromethane)

Sources & evidence

ORD record
ord-58a1d8348ac846efa7527d8089ba363b
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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