Sodium Carbonate → (4-Tert-butoxycarbonylamino-2'-trifluoromethanesulfonyl-biphenyl-3-yl)-carbamic acid tert-butyl ester

HRID 1433222Notes

Reaction equation

[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1[CH:13]=[CH:12][C:11](B2OC(C)(C)C(C)(C)O2)=[CH:10][C:9]=1[NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])([CH3:4])([CH3:3])[CH3:2].Cl[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[S:39]([C:42]([F:45])([F:44])[F:43])(=[O:41])=[O:40].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[C:27]([O:26][C:24](=[O:25])[NH:23][C:9]1[CH:10]=[C:11]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[S:39]([C:42]([F:43])([F:44])[F:45])(=[O:40])=[O:41])[CH:12]=[CH:13][C:8]=1[NH:7][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:31])([CH3:30])([CH3:29])[CH3:28]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of [2-tert-butoxycarbonylamino-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-carbamic acid tert-butyl ester (0.213 g, 0.490 mmol), 1-chloro-2-trifluoromethanesulfonyl-benzene (0.100 g, 0.409 mmol), sodium carbonate (0.260 g, 2.45 mmol), and 1,1′-[bis(di-tert-butylphosphino)ferrocene]-palladium dichloride (0.027 g, 0.0409 mmol) in DME (2 mL) and H2O (0.5 mL) was heated at 90° C. for 12 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by chromatography (silica, hexanes: EtOAc, 1:1) to afford the title compound as a yellow solid (0.158 g, 75%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by chromatography (silica, hexanes: EtOAc, 1:1)

Sources & evidence

ORD record: ord-5e3c4d58f1024536899930f84f76acc4
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612211B2

Reaction notes

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