Cesium carbonate → 854514-88-8

HRID 2078465Notes

Reaction equation

HRID 2078465 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.C([O-])([O-])=O.[Cs+].[Cs+].[OH:16][C:17]1[CH:26]=[C:25]2[C:20]([C:21]([O:27][C:28]3[CH:41]=[CH:40][C:31]4[C:32]([C:36]([NH:38][CH3:39])=[O:37])=[C:33]([CH3:35])[O:34][C:30]=4[CH:29]=3)=[CH:22][CH:23]=[N:24]2)=[CH:19][CH:18]=1>CC#N>[CH3:39][NH:38][C:36]([C:32]1[C:31]2[CH:40]=[CH:41][C:28]([O:27][C:21]3[C:20]4[C:25](=[CH:26][C:17]([O:16][CH2:2][CH2:3][N:4]5[CH2:9][CH2:8][O:7][CH2:6][CH2:5]5)=[CH:18][CH:19]=4)[N:24]=[CH:23][CH:22]=3)=[CH:29][C:30]=2[O:34][C:33]=1[CH3:35])=[O:37]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 767274-(2-Chloroethyl)morpholineHCID 135507449HCID 135507449, compound

Product 1

HCID 11236560854514-88-8Yield 67.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(2-chloroethyl)morpholine (2.1 g, 11.5 mmol) and Cs2CO3 (7.5 g, 23 mmol) in CH3CN (100 mL) was stirred for 45 minutes at room temperature. To the solution was added 6-[(7-hydroxyquinolin-4-yl)oxy]-N,2-dimethyl-1-benzofuran-3-carboxamide (2 g, 5.75 mmol). The mixture was heated to reflux for 3 hrs. Inorganic salt was removed by filtration and the solution was concentrated. The residue was purified by a silica gel column chromatography (using 1 to 10% MeOH/CH2Cl2) to give 1.8 g of free base N,2-dimethyl-6-[7-(2-morpholinoethoxy)quinolin-4-yloxy]benzofuran-3-carboxamide as a solid. The compound was then dissolved in hot isopropanol and stirred at room temperature overnight. 1.13 g of N,2-dimethyl-6-[7-(2-morpholinoethoxy)quinolin-4-yloxy]benzofuran-3-carboxamide as polymorph Form 2 was collected by filtration. Note, Form 2 is anhydrous and must be prepared under water-free conditions in order to prevent hydrate formation (such as Form 4 as described in Example 6).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hrs
  3. customInorganic salt was removed by filtration
  4. concentrationthe solution was concentrated
  5. customThe residue was purified by a silica gel column chromatography (using 1 to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-af4e91128eba404ab4a533bf1c24a8c2
Source dataset
uspto-grants-2011_04
Patent number
US07928226B2

Reaction notes

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