Potassium Carbonate → HCID 86681728, compound

HRID 571318Notes

Reaction equation

HRID 571318 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:10]=[CH:9]2)(=[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:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[N:11]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:10]=[CH:9]3)[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 86681621HCID 86681621, compound

Product 1

HCID 86681728HCID 86681728, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 2-(5-(methylsulfonamido)-1H-indol-1-yl)acetate (1.8 g, 6.38 mmol) (prepared in an analogous manner as described in, Example 14, Scheme 14, Steps 1, 2, 3) in CH3CN (30 ml), K2CO3 (1.762 g, 12.75 mmol) and 4-(2-chloroethyl)morpholine hydrochloride (1.186 g, 6.38 mmol) were added, and the mixture heated to reflux for 3 hours. The solvent was removed and the residue was purified by flash chromatography on silica gel (DCM/MeOH 99:1 to 97:3) recovering methyl 2-(5-(N-(2-morpholinoethyl)methylsulfonamido)-1H-indol-1-yl)acetate (1.5 g, 3.79 mmol, 59.5% yield, UPLC-MS purity: 96%, MS/ESI+ 396.2 [MH]+).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 3 hours
  3. customThe solvent was removed
  4. customthe residue was purified by flash chromatography on silica gel (DCM/MeOH 99:1 to 97:3)

Sources & evidence

ORD record
ord-85784e100b004f0881624a5cb5858f2d
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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