Butyl isocyanate → HCID 54043146, compound

HRID 1029733Notes

Reaction equation

HRID 1029733 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:32]=[C:33]=[O:34])[CH2:29][CH2:30][CH3:31]>O1CCCC1>[CH2:28]([NH:32][C:33](=[O:34])[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])[CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 8110Butyl isocyanateHCID 11430Potassium CarbonateHCID 190723493-Methyl-1-[propyl(pyridin-4-yl)amino]-1H-indol-5-ol

Product 1

HCID 54043146HCID 54043146, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution consisting of 3-methyl-1-(propyl-4-pyridinylamino)-1H-indol-5-ol (2.11 g) and tetrahydrofuran (50 ml) was added milled K2CO3 (1.09 g), followed by dropwise addition of butyl isocyanate (0.93 ml) at room temperature under nitrogen. Stirring was continued for 2.0 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 2.65 g of the desired carbamate as an oil. This oil was dissolved in a small amount of EtOAc and diluted with ether, whereupon the product crystallized as a white powder, m.p. 120°-122° 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-1789c13dc0fe425fa73534cc70e03c96
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

Loading…