Cesium carbonate → HCID 67111153, compound

HRID 2363187Notes

Reaction equation

HRID 2363187 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6](B3OC(C)(C)C(C)(C)O3)[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=2)[CH2:3][CH2:2]1.[F:23][C:24]1[CH:25]=[C:26]([CH:36]([NH:38][C:39]([C:41]2[O:42][C:43](Br)=[CH:44][CH:45]=2)=[O:40])[CH3:37])[CH:27]=[C:28]([F:35])[C:29]=1[NH:30][S:31]([CH3:34])(=[O:33])=[O:32].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:24]1[CH:25]=[C:26]([CH:36]([NH:38][C:39]([C:41]2[O:42][C:43]([C:6]3[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=[C:4]([CH:1]4[CH2:2][CH2:3]4)[CH:5]=3)=[CH:44][CH:45]=2)=[O:40])[CH3:37])[CH:27]=[C:28]([F:35])[C:29]=1[NH:30][S:31]([CH3:34])(=[O:33])=[O:32]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 58319279HCID 58319279, compoundHCID 67111141HCID 67111141, compound

Product 1

HCID 67111153HCID 67111153, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

2-(3-Cyclopropyl-5-trifluoromethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (120 mg, 0.26 mmol) and 5-Bromo-furan-2-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide (110 mg, 0.26 mmol) was reacted using Pd(PPh3)2Cl2 (18 mg, 0.03 mmol), Cs2CO3 (250 mg, 0.77 mmol) as described in example 102 to give the title compound (25 mg, 18%) after purification by flash chromatography on silica gel (hexane: EtOAc=1:1).

Sources & evidence

ORD record
ord-a5d6a2d2167d4dbcb28df16fc7d96d36
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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