Cesium carbonate → HCID 67238640, compound

HRID 2363175Notes

Reaction equation

HRID 2363175 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.[F:11][C:12]1[CH:13]=[C:14]([CH:24]([NH:26][C:27]([C:29]2[N:30]=[C:31](Cl)[O:32][CH:33]=2)=[O:28])[CH3:25])[CH:15]=[C:16]([F:23])[C:17]=1[NH:18][S:19]([CH3:22])(=[O:21])=[O:20].C([O-])([O-])=O.[Cs+].[Cs+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:23][C:16]1[CH:15]=[C:14]([CH:24]([NH:26][C:27]([C:29]2[N:30]=[C:31]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[O:32][CH:33]=2)=[O:28])[CH3:25])[CH:13]=[C:12]([F:11])[C:17]=1[NH:18][S:19]([CH3:22])(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27343222-Chlorophenylboronic acidHCID 671108872-Chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide

Product 1

HCID 67238640HCID 67238640, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

2-Chlorophenylboronic acid (40.7 mg, 0.26 mmol) and 2-chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide (50 mg, 0.13 mmol) was reacted using Pd(PPh3)2Cl2 (7 mg, 0.01 mmol), Cs2CO3 (127 mg, 0.39 mmol) as described above to give the title compound (18 mg, 30%) after purification by flash chromatography on silica gel (hexane: EtOAc=1:1).

Sources & evidence

ORD record
ord-9079bb9d070b406592b1b8e446d57ec0
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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