Cesium carbonate → HCID 44603390, compound

HRID 2363199Notes

Reaction equation

HRID 2363199 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5](B2OC(C)(C)C(C)(C)O2)[CH:6]=[C:7]([CH:9]=[CH2:10])[CH:8]=1.[F:22][C:23]1[CH:24]=[C:25]([CH:35]([NH:37][C:38]([C:40]2[O:41][C:42](Br)=[CH:43][CH:44]=2)=[O:39])[CH3:36])[CH:26]=[C:27]([F:34])[C:28]=1[NH:29][S:30]([CH3:33])(=[O:32])=[O:31].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:22][C:23]1[CH:24]=[C:25]([CH:35]([NH:37][C:38]([C:40]2[O:41][C:42]([C:5]3[CH:6]=[C:7]([CH:9]=[CH2:10])[CH:8]=[C:3]([C:2]([F:1])([F:20])[F:21])[CH:4]=3)=[CH:43][CH:44]=2)=[O:39])[CH3:36])[CH:26]=[C:27]([F:34])[C:28]=1[NH:29][S:30]([CH3:33])(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 58319306HCID 58319306, compoundHCID 67111141HCID 67111141, compound

Product 1

HCID 44603390HCID 44603390, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

2-(3-Trifluoromethyl-5-vinyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (135 mg, 0.45 mmol) and 5-bromo-furan-2-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide (130 mg, 0.31 mmol) was reacted using Pd(PPh3)2Cl2 (20 mg, 0.03 mmol), Cs2CO3 (300 mg, 0.92 mmol) as described above to give the title compound (100 mg, 63%) after purification by flash chromatography on silica gel (hexane: EtOAc=1:1).

Sources & evidence

ORD record
ord-2dcce87174b148289ca7134602d8e128
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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