Cesium carbonate → HCID 58149025, compound

HRID 1810460Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]([CH2:14][C:15]1[CH:20]=[C:19]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:18]=[CH:17][C:16]=1OS(C(F)(F)F)(=O)=O)[CH2:12][CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:33]([O:35][C:36](=[O:55])[CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[C:40](B2OC(C)(C)C(C)(C)O2)[CH:39]=1)[CH3:34].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:33]([O:35][C:36](=[O:55])[CH2:37][C:38]1[CH:39]=[C:40]([C:16]2[CH:17]=[CH:18][C:19]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:20][C:15]=2[CH2:14][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:12][CH3:13])[C:41]([O:44][CH3:45])=[CH:42][CH:43]=1)[CH3:34]

Participants

Conditions

Temperature: 45 °C

Procedure

Trifluoro-methanesulfonic acid 2-[(benzyloxycarbonyl-ethyl-amino)-methyl]-4-methanesulfonyl-phenyl ester (1.3 g, 2.62 mmol), [4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl ester (1.26 g, 3.93 mmol), and cesium carbonate (2.55 g, 7.85 mmol) were combined in DMF. (1,1′-Bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.213 g, 0.26 mmol) was added, and the reaction was immediately immersed in an oil bath pre-heated to 45° C. The reaction was stirred at 65° C. for 20 minutes, and then worked-up and purified to give the title compound, contaminated with a phenol by-product. The mixture was dissolved in CH2Cl2 (100 mL) and washed with 0.5N aqueous NaOH, and then concentrated to give the title compound.

Workup

customthe reaction was immediately immersed in an oil bath
custompurified

Sources & evidence

ORD record: ord-a0eb8e10cb3140a592edac2eba46ed3c
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362044B2

Reaction notes

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