Cesium carbonate → HCID 67238701, compound

HRID 2363196Notes

Reaction equation

HRID 2363196 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6](B3OC(C)(C)C(C)(C)O3)[CH:7]=[C:8]([CH:10]3[CH2:12][CH2:11]3)[CH:9]=2)[CH2:3][CH2:2]1.[F:22][C:23]1[CH:24]=[C:25]([CH:35]([NH:37][C:38]([C:40]2[N:41]=[C:42](Cl)[S: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:34][C:27]1[CH:26]=[C:25]([CH:35]([NH:37][C:38]([C:40]2[N:41]=[C:42]([C:6]3[CH:7]=[C:8]([CH:10]4[CH2:11][CH2:12]4)[CH:9]=[C:4]([CH:1]4[CH2:2][CH2:3]4)[CH:5]=3)[S:43][CH:44]=2)=[O:39])[CH3:36])[CH:24]=[C:23]([F:22])[C:28]=1[NH:29][S:30]([CH3:33])(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 58319249HCID 58319249, compoundHCID 67110925HCID 67110925, compound

Product 1

HCID 67238701HCID 67238701, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

2-(3,5-Dicyclopropyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (74 mg, 0.26 mmol) and 2-chloro-thiazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide (110 mg, 0.26 mmol) was reacted using Pd(PPh3)2Cl2 (14 mg, 0.02 mmol), Cs2CO3 (254 mg, 0.78 mmol) as described above to give the title compound (22 mg, 16%) after purification by flash chromatography on silica gel (% EtOAc′ in hexane=30%˜70%).

Sources & evidence

ORD record
ord-0ee8a8e178f94793b1b35b8fdb63a142
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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