Dichloromethane → 1,1-Dimethylethyl (2-{[3'-(aminocarbonyl)-2-methyl-4-biphenylyl]oxy}ethyl)carbamate

HRID 471849Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][C:3]=1[CH3:19].[NH2:20][C:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)=[O:22].C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].COCCOC>[NH2:20][C:21]([C:23]1[CH:28]=[C:27]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][C:3]=2[CH3:19])[CH:26]=[CH:25][CH:24]=1)=[O:22]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1,1-dimethylethyl {2-[(4-bromo-3-methylphenyl)oxy]ethyl}carbamate (0.102 g, 0.31 mmol; Example V-15), 3-(aminocarbonyl)phenylboronic acid (0.056 g; 0.34 mmol), PdCl2(dppf).CH2Cl2 (0.0075 g; 0.01 mmol), DME (2 mL) and 2M Na2CO3 (2 mL) was degassed by sparging with N2, (5-10 min) then stirred at 80° C. for 5.5 h. Upon cooling, the mixture was diluted with EtOAc washed (water, brine), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless foam. LC/MS (method A) 2.59 min, m/z 371 (M+1, 2%), 392 (M+Na, 53%), 271 ([M−Boc]+H, 100%).

Workup

customby sparging with N2, (5-10 min)
temperatureUpon cooling
additionthe mixture was diluted with EtOAc
washwashed (water, brine)
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record: ord-5f0c75d69cfe41379da794e3c7d0d140
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633175B2

Reaction notes

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