Potassium Carbonate → HCID 54516609, compound

HRID 1029716Notes

Reaction equation

HRID 1029716 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+].[CH3:27][N:28]=[C:29]=[O:30]>O1CCCC1>[CH3:27][NH:28][C:29](=[O:30])[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

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 18960815HCID 18960815, compound

Product 1

HCID 54516609HCID 54516609, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2.5 g of 1-(propyl-4-pyridinylamino)-1H-indol-5-ol in 30 ml of tetrahydrofuran was added potassium carbonate (milled, 1.3 g) followed by methyl isocyanate (0.56 ml). The reaction was allowed to proceed for half an hour. The reaction mixture was then filtered and the filtrate concentrated to yield a solid (2.9 g) which was eluted with 5% methanol in dichloromethane on a silica gel column via HPLC. The desired fractions were concentrated to yield a solid (2.7 g) which was recrystallized from isopropyl ether to yield a solid 1.8 g, m.p. 158°-159° C.

Workup

  1. waitto proceed for half an hour
  2. filtrationThe reaction mixture was then filtered
  3. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-6e2fe685dc5d402d85adad283980c22e
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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