Cesium carbonate → HCID 44603250, compound

HRID 2363192Notes

Reaction equation

HRID 2363192 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([CH:10]3OC(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[N:38]=C(Cl)[S: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:31][C:24]1[CH:23]=[C:22]([CH:32]([NH:34][C:35]([C:37]2[N:38]=[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([CH:1]4[CH2:2][CH2:3]4)[CH:5]=3)[S:40][CH:41]=2)=[O:36])[CH3:33])[CH:21]=[C:20]([F:19])[C:25]=1[NH:26][S:27]([CH3:30])(=[O:28])=[O:29]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 67110925HCID 67110925, compoundHCID 67111193HCID 67111193, compound

Product 1

HCID 44603250HCID 44603250, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

2-(3-Cyclopropyl-phenyl)-4,4,5,5-tetramethyl-[1,3]dioxolane (63 mg, 0.26 mmol) and 2-chloro-thiazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide (55 mg, 0.13 mmol) was reacted using Pd(PPh3)2Cl2 (7 mg, 0.01 mmol), Cs2CO3 (127 mg, 0.39 mmol) as described above to give the title compound (23 mg, 38%) after purification by flash chromatography on silica gel (% EtOAc in hexane=25%˜100%).

Sources & evidence

ORD record
ord-c689e4aa99f24ac1852e9f71264dabcd
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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