Potassium Carbonate → HCID 21959415, compound

HRID 887588Notes

Reaction equation

HRID 887588 reaction equation
C([O-])([O-])=O.[K+].[K+].[N+:7]([C:10]1[CH:18]=[C:17]2[C:13]([CH:14]=[CH:15][NH:16]2)=[CH:12][CH:11]=1)([O-])=O.Cl.Cl[CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>CC#N>[N:23]1([CH2:22][CH2:21][N:16]2[C:17]3[C:13](=[CH:12][CH:11]=[C:10]([NH2:7])[CH:18]=3)[CH:14]=[CH:15]2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 785026-Nitro-1H-indole

Product 1

HCID 21959415HCID 21959415, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

K2CO3 (5.08 g, 36.726 mmol) was added to a slurry of 6-nitroindole (1.985 g, 12.242 mmol), 4-(2-chloroethyl) morpholine HCl (2.278 g, 12.242 mmol), and CH3CN (100 ml). The mix was heated to reflux for 18 h, then cooled to RT, filtered, and concentrated in vacuo. The crude was eluted through a silica gel column with a gradient of 3:97 to 5:95 and finally 8:92 MeOH/CH2Cl2, to yield upon drying the desired intermediate which was hydrogenated under conditions previously described.

Workup

  1. temperatureThe mix was heated
  2. temperatureto reflux for 18 h
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washThe crude was eluted through a silica gel column with a gradient of 3:97 to 5:95 and finally 8:92 MeOH/CH2Cl2
  6. customto yield
  7. dry with materialupon drying the desired intermediate which

Sources & evidence

ORD record
ord-8ffb013676fd40ad90506105cda947e3
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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