Cesium carbonate → HCID 58149025, compound

HRID 2197380Notes

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-c3fe4fd8c68f4088bfc83dce63d7986c
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338484B2

Reaction notes

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