Potassium Carbonate → HCID 9888022, compound

HRID 1029722Notes

Reaction equation

HRID 1029722 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:21](=O)([O-])[O-].[K+].[K+].C[C@:28]1([CH:37]=[CH:36][CH:35]=[CH:34][CH2:33]1)[CH2:29][N:30]=[C:31]=[O:32]>O1CCCC1>[C:28]1([C@@H:29]([NH:30][C:31](=[O:32])[O:14][C:10]2[CH:9]=[C:8]3[C:13](=[CH:12][CH:11]=2)[N:5]([N:4]([CH2:1][CH2:2][CH3:3])[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH:6]=[CH:7]3)[CH3:21])[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18960815HCID 18960815, compoundHCID 86745639HCID 86745639, compound

Product 1

HCID 9888022HCID 9888022, compoundYield 144.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1-(propyl-4-pyridinylamino)-1H-indol-5-ol (1.75 g) in 30 ml of tetrahydrofuran was added potassium carbonate (milled, 0.912 g) followed by (S)-(-)-1-methylbenzyl isocyanate (0.97 g), and the reaction was allowed to proceed for one hour. The reaction mixture was filtered and the filtrate concentrated to yield an oil (3.9 g) which was eluted with 5% methanol in dichloromethane (DCM) on a silica gel column via HPLC. The desired fractions were concentrated to yield a solid 2.6 g, m.p. 78°-80° C.

Workup

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

Sources & evidence

ORD record
ord-594c692826e84b28aadee7e3d791909e
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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