Potassium Carbonate → HCID 54145909, compound

HRID 1029718Notes

Reaction equation

HRID 1029718 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+].[CH:27]([N:30]=[C:31]=[O:32])([CH3:29])[CH3:28]>O1CCCC1>[CH: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)([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 61277Isopropyl isocyanateHCID 18960815HCID 18960815, compound

Product 1

HCID 54145909HCID 54145909, compoundYield 115.6%

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 isopropyl isocyanate (0.67 g) was added and the reaction mixture was stirred for 4 hours. The mixture was filtered and the filtrate was concentrated to yield a solid (3.2 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 (2.75 g), m.p. 131°-133° C.

Workup

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

Sources & evidence

ORD record
ord-9efc327c646e48d3a6c5ca701b0ecc6d
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

Loading…