Cesium carbonate → HCID 44603251, compound

HRID 2363193Notes

Reaction equation

HRID 2363193 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6](C3OC(C)(C)C(C)(C)O3)[CH:7]=[CH:8][CH:9]=2)[CH2:3][CH2:2]1.[F:19][C:20]1[CH:21]=[C:22]([CH:32]([NH:34][C:35]([C:37]2[O:38][C:39](Br)=[CH:40][CH:41]=2)=[O:36])[CH3:33])[CH:23]=[C:24]([F:31])[C:25]=1[NH:26][S:27]([CH3:30])(=[O:29])=[O:28].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:19][C:20]1[CH:21]=[C:22]([CH:32]([NH:34][C:35]([C:37]2[O:38][C:39]([C:8]3[CH:7]=[CH:6][CH:5]=[C:4]([CH:1]4[CH2:3][CH2:2]4)[CH:9]=3)=[CH:40][CH:41]=2)=[O:36])[CH3:33])[CH:23]=[C:24]([F:31])[C:25]=1[NH:26][S:27]([CH3:30])(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 67111141HCID 67111141, compoundHCID 67111193HCID 67111193, compound

Product 1

HCID 44603251HCID 44603251, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

2-(3-Cyclopropyl-phenyl)-4,4,5,5-tetramethyl-[1,3]dioxolane (126 mg, 0.52 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 (14 mg, 0.02 mmol), Cs2CO3 (254 mg, 0.78 mmol) as described above to give the title compound (54 mg, 56%) after purification by recrystallization from n-Hex/EtOAc.

Sources & evidence

ORD record
ord-46aa04f2f0cf49a2a3bad35a6ab0c261
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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