Cesium carbonate → HCID 44603189, compound

HRID 2363178Notes

Reaction equation

HRID 2363178 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[F:18][C:19]1[CH:20]=[C:21]([CH:31]([NH:33][C:34]([C:36]2[N:37]=[C:38](Cl)[O:39][CH:40]=2)=[O:35])[CH3:32])[CH:22]=[C:23]([F:30])[C:24]=1[NH:25][S:26]([CH3:29])(=[O:28])=[O:27].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:30][C:23]1[CH:22]=[C:21]([CH:31]([NH:33][C:34]([C:36]2[N:37]=[C:38]([C:5]3[CH:4]=[C:3]([C:2]([F:17])([F:16])[F:1])[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=3)[O:39][CH:40]=2)=[O:35])[CH3:32])[CH:20]=[C:19]([F:18])[C:24]=1[NH:25][S:26]([CH3:29])(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1562653,5-Bis-trifluoromethylphenylboronic acidHCID 671108872-Chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide

Product 1

HCID 44603189HCID 44603189, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

3,5-Bis(trifluoromethyl)benzeneboronic acid (67 mg, 0.26 mmol) and 2-chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylaminophenyl)-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 (14 mg, 19%) after purification by flash chromatography on silica gel (% EtOAc in hexane=12%˜80%).

Sources & evidence

ORD record
ord-fcc410975ddb449799cd8db603ad76e2
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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