Cesium carbonate → 3-[(2-Fluoro-4-iodophenyl)amino]-5-[(2-oxo-2,3-dihydro-1,3-benzoxazol-5-yl)oxy]isonicotinamide

HRID 2167221Notes

Reaction equation

F[C:2]1[CH:10]=[N:9][CH:8]=[C:7]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([I:18])=[CH:14][C:13]=2[F:19])[C:3]=1[C:4]([NH2:6])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].[OH:26][C:27]1[CH:28]=[CH:29][C:30]2[O:34][C:33](=[O:35])[NH:32][C:31]=2[CH:36]=1>CN(C=O)C>[F:19][C:13]1[CH:14]=[C:15]([I:18])[CH:16]=[CH:17][C:12]=1[NH:11][C:7]1[CH:8]=[N:9][CH:10]=[C:2]([O:26][C:27]2[CH:28]=[CH:29][C:30]3[O:34][C:33](=[O:35])[NH:32][C:31]=3[CH:36]=2)[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

Conditions

Temperature: 50 °C

Procedure

100 mg of 3-fluoro-5-[(2-fluoro-4-iodophenyl)amino]isonicotinamide (0.251 mmol, 1. eq.) were dissolved in DMF under a nitrogen atmosphere, then 245 mg of cesium carbonate (0.752 mmol, 3 eq.) and 45 mg of 5-hydroxy-1,3-benzoxazol-2(3H)-one (0.301 mmol, 1.2 eq.) were added. The resulting mixture was stirred at 50° C. bath temperature for 3 days. Then the mixture was partitioned between aq. NH4Cl solution (30 ml) and dichloromethane (30 ml). The phases were separated and the aqueouse layer was reextracted twice with dichloromethane/isopropanole (4:1, 30 ml each).

Workup

customThen the mixture was partitioned between aq. NH4Cl solution (30 ml) and dichloromethane (30 ml)
customThe phases were separated

Sources & evidence

ORD record: ord-c512018f990b46a890617a31dc9e63a6
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045429B2

Reaction notes

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