Cesium carbonate → HCID 58149025, compound

HRID 1920019Notes

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-e83472a3c0dc434fa6210200749e9ac0
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168678B2

Reaction notes

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