Cesium carbonate → 854514-88-8

HRID 2078464Notes

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>CN(C=O)C>[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

Conditions

Temperature: 120 °C

Procedure

A solution of 4-(2-chloroethyl)morpholine (10.7 g, 57.4 mmol) and Cs2CO3 (46.3 g, 143.5 mmol) in DMF (100 mL) was stirred for 1 hour at room temperature. To the solution was added a solution of 6-[(7-hydroxyquinolin-4-yl)oxy]-N,2-dimethyl-1-benzofuran-3-carboxamide (10 g, 28.7 mmol). The mixture was heated to 120° C. for 15 hr. The solution was cooled to room temperature and extracted with EtOAc. The concentrated residue was purified by a silica gel column chromatography (using 5 to 10%) MeOH/CH2Cl2) to give 2.6 g of free base N,2-dimethyl-6-[7-(2-morpholinoethoxy)quinolin-4-yloxy]benzofuran-3-carboxamide as a solid. The solid free base was identified as Form 1 as characterized by powder X-ray diffraction as shown in FIG. 11. Note, Form 1 can also be prepared by slurrying any of Forms 3, 5, or 6 in water at room temperature for 24 hours.

Workup

temperatureThe solution was cooled to room temperature
extractionextracted with EtOAc
customThe concentrated residue was purified by a silica gel column chromatography (using 5 to 10%) MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-06a8a6d835494f30abce65f4b4042bea
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928226B2

Reaction notes

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