Potassium Carbonate → HCID 67618062, compound

HRID 1029714Notes

Reaction equation

HRID 1029714 reaction equation
[CH2:1]([N:8]=[C:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:11][N:12]([C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)[N:13]1[C:21]2[C:16](=[CH:17][C:18]([OH:22])=[CH:19][CH:20]=2)[CH:15]=[CH:14]1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[C:2]1([CH2:1][NH:8][C:9](=[O:10])[O:22][C:18]2[CH:17]=[C:16]3[C:21](=[CH:20][CH:19]=2)[N:13]([N:12]([CH3:11])[C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[CH:14]=[CH:15]3)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76639Benzyl isocyanateHCID 19900479HCID 19900479, compound

Product 1

HCID 67618062HCID 67618062, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl isocyanate (1.7 g) was added to a solution of 1-(methyl-4-pyridinylamino)-1H-indol-5-ol (2.5 g) in 75 mL tetrahydrofuran containing potassium carbonate (milled, 3 g). After stirring three hours at ambient temperature the mixture was filtered and concentrated. The residue was eluted through silica with ethyl acetate via flash column chromatography to yield 3.8 g solid. This was recrystallized from acetonitrile to yield 3.2 g crystals, m.p. 179°-181° C.

Workup

  1. filtrationwas filtered
  2. concentrationconcentrated
  3. washThe residue was eluted through silica with ethyl acetate via flash column chromatography

Sources & evidence

ORD record
ord-979f61f67a9d4275b5a67bfc59dc0a7e
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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