Cesium carbonate → HCID 67238130, compound

HRID 2363173Notes

Reaction equation

HRID 2363173 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.[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:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[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 2734323(3-Chlorophenyl)boronic acidHCID 671108872-Chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide

Product 1

HCID 67238130HCID 67238130, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

3-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 (20 mg, 34%) after purification by flash chromatography on silica gel (hexane: EtOAc=1:1). 1H NMR (300 MHz, CDCl3): δ8.31 (s, 1H), 8.05 (s, 1H), 7.93 (d, 1H, J=7.2 Hz), 7.45 (m, 2H), 7.29 (bs, 1H), 7.01 (d, 2H, J=8.7 Hz), 6.67 (s, 1H), 5.22 (m, 1H), 3.18 (s, 3H), 1.60 (d, 3H, J=6.9 Hz)

Sources & evidence

ORD record
ord-6358d7ac713b4f2997b0699f89abe827
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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