Potassium Carbonate → HCID 67618171, compound

HRID 1029720Notes

Reaction equation

HRID 1029720 reaction equation
[CH2:1]([N:8]=[C:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:11]([N:14]([C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1)[N:15]1[C:23]2[C:18](=[CH:19][C:20]([OH:24])=[CH:21][CH:22]=2)[CH:17]=[CH:16]1)[CH2:12][CH3:13].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[C:2]1([CH2:1][NH:8][C:9](=[O:10])[O:24][C:20]2[CH:19]=[C:18]3[C:23](=[CH:22][CH:21]=2)[N:15]([N:14]([CH2:11][CH2:12][CH3:13])[C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH:16]=[CH:17]3)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76639Benzyl isocyanateHCID 18960815HCID 18960815, compound

Product 1

HCID 67618171HCID 67618171, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl isocyanate (2 g) was added to a solution of 1-(propyl-4-pyridinylamino)-1H-indol-5-ol (3.3 g) in 75 mL tetrahydrofuran containing potassium carbonate (milled, 3 g). After stirring twenty hours at ambient temperature, the mixture was filtered and the filtrate was concentrated. The residue was eluted through silica with ethyl acetate via flash column chromatography to yield 5 g of the product as a solid, m.p. 156°-158° C. The product was recrystallized from acetonitrile to yield 3.8 g of crystals, m.p. 162°-164° C.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. washThe residue was eluted through silica with ethyl acetate via flash column chromatography

Sources & evidence

ORD record
ord-0a0f0f952880480f9c2888aa6e220a1c
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

Loading…