Potassium Carbonate → HCID 86681733, compound

HRID 571320Notes

Reaction equation

HRID 571320 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][N:10]2[CH2:15][C:16]([O:18][CH3:19])=[O:17])(=[O:4])=[O:3].C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>CC#N>[O:33]1[CH2:34][CH2:35][N:30]([CH2:29][CH2:28][N:5]([C:6]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:7]=2[CH:8]=[CH:9][N:10]3[CH2:15][C:16]([O:18][CH3:19])=[O:17])[S:2]([CH3:1])(=[O:3])=[O:4])[CH2:31][CH2:32]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 86681628HCID 86681628, compound

Product 1

HCID 86681733HCID 86681733, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 2-(4-(methylsulfonamido)-1H-indol-1-yl)acetate (1.0 g, 3.54 mmol) (prepared in an analogous manner as described Example 15, Scheme 15, Steps 1, 2, 3) in CH3CN (30 ml), K2CO3 (0.734 g, 5.31 mmol) and 4-(2-chloroethyl)-morpholine hydrochloride (0.989 g, 5.31 mmol) were added, and the resulting mixture heated to reflux for 3 hours. The insoluble inorganic salts were filtered off and the filtrate was evaporated to dryness affording methyl 2-(4-(N-(2-morpholinoethyl)-methylsulfonamido)-1H-indol-1-yl)acetate (1.08 g, 2.73 mmol, 77% yield, MS/ESI+ 395.9 [MH]+) which was used without any additional purification.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureto reflux for 3 hours
  3. filtrationThe insoluble inorganic salts were filtered off
  4. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-ce1ddc771b7244cf8414be3159a51abf
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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