Potassium Carbonate → HCID 53867360, compound

HRID 1029717Notes

Reaction equation

HRID 1029717 reaction equation
[CH2:1]([N:4]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)[N:5]1[C:13]2[C:8](=[CH:9][C:10]([OH:14])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH2:27]([N:30]=[C:31]=[O:32])[CH2:28][CH3:29]>O1CCCC1>[CH2:27]([NH:30][C:31](=[O:32])[O:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([N:4]([CH2:1][CH2:2][CH3:3])[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)[CH:6]=[CH:7]2)[CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 61033Propyl isocyanateHCID 18960815HCID 18960815, compound

Product 1

HCID 53867360HCID 53867360, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(propyl-4-pyridinylamino)-1H-indol-5-ol (2.1 g) in 50 ml of tetrahydrofuran was added potassium carbonate (milled, 1.3 g). Then propyl isocyanate (0.67 g) was added and the reaction mixture was stirred for 2 hours. The mixture was filtered and the filtrate was concentrated to yield an oil (2.8 g), which was eluted with 5% methanol/dichloromethane on a silica gel column via HPLC. The desired fractions were concentrated to yield an oil which solidified on standing (2.5 g), m.p. 120°-122° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0490beaf4225425cbb24dae0d32e9d69
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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