Cesium carbonate → HCID 44603248, compound

HRID 2363185Notes

Reaction equation

HRID 2363185 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.[F:14][C:15]1[CH:16]=[C:17]([CH:27]([NH:29][C:30]([C:32]2[N:33]=[C:34](Cl)[S:35][CH:36]=2)=[O:31])[CH3:28])[CH:18]=[C:19]([F:26])[C:20]=1[NH:21][S:22]([CH3:25])(=[O:24])=[O:23].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:26][C:19]1[CH:18]=[C:17]([CH:27]([NH:29][C:30]([C:32]2[N:33]=[C:34]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:13])([F:12])[F:1])[CH:4]=3)[S:35][CH:36]=2)=[O:31])[CH3:28])[CH:16]=[C:15]([F:14])[C:20]=1[NH:21][S:22]([CH3:25])(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 67110925HCID 67110925, compound

Product 1

HCID 44603248HCID 44603248, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

3-Trifluoromethylphenylboronic acid (62.7 mg, 0.33 mmol) and 2-chloro-thiazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide (44.6 mg, 0.11 mmol) was reacted using Pd(PPh3)2Cl2 (10.5 mg, 0.015 mmol), Cs2CO3 (143.4 mg, 0.44 mmol) as described above to give the title compound (29 mg, 44%) after purification by flash chromatography on silica gel (hexane: EtOAc=1:1).

Sources & evidence

ORD record
ord-39ffd3bb2f4a418285f668d239913d0c
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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