Sodium Carbonate → [4-Tert-butoxycarbonylamino-2'-(2-hydroxy-ethanesulfonyl)-biphenyl-3-yl]-carbamic acid tert-butyl ester

HRID 1433226Notes

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].Br[CH2:33][CH:34]([S:36]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)(=[O:38])=[O:37])O.C(=O)([O-])[O-:46].[Na+].[Na+]>COCCOC.O>[C:27]([O:26][C:24](=[O:25])[NH:23][C:9]1[CH:10]=[C:11]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2[S:36]([CH2:34][CH2:33][OH:46])(=[O:38])=[O:37])[CH:12]=[CH:13][C:8]=1[NH:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:31])([CH3:29])([CH3:28])[CH3:30]

Participants

Conditions

Temperature: 100 °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 (0.300 g, 0.691 mmol, Example 15, Step A), 2-bromophenylsulfonylethanol (0.153 g, 0.576 mmol), sodium carbonate (0.439 g, 4.15 mmol), and 1,1′-[bis(di-tert-butylphosphino)ferrocene]-palladium dichloride (0.153 g, 0.0576 mmol) in DME (6 mL) and H2O (1.5 mL) was heated at 100° C. for 12 hours. The reaction mixture was concentrated under reduced pressure to provide a residue, which was purified by chromatography (silica, hexanes:EtOAc, 1:1) to afford the title compound as a yellow oil (0.233 g, 82%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customto provide a residue, which
customwas purified by chromatography (silica, hexanes:EtOAc, 1:1)

Sources & evidence

ORD record: ord-f3f4ef4c323645cb87353de394be8875
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612211B2

Reaction notes

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