Cesium carbonate → (4'-Chloro-3,5-diethylbiphen-4-yl)carbamic acid

HRID 341691Notes

Reaction equation

HRID 341691 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].C([O:11][C:12](=[O:25])[NH:13][C:14]1[C:19]([CH2:20][CH3:21])=[CH:18][C:17](Br)=[CH:16][C:15]=1[CH2:23][CH3:24])(C)(C)C.[Cl:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>O.CC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([C:17]2[CH:16]=[C:15]([CH2:23][CH3:24])[C:14]([NH:13][C:12](=[O:25])[OH:11])=[C:19]([CH2:20][CH3:21])[CH:18]=2)=[CH:29][CH:28]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 742994-Chlorophenylboronic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 59450511tert-Butyl (4-bromo-2,6-diethylphenyl)carbamate

Product 1

HCID 131732100(4'-Chloro-3,5-diethylbiphen-4-yl)carbamic acid

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of cesium carbonate (89.12 g, 0.27 mol) in water (600 ml) is added to a degassed solution of (4-bromo-2,6-diethylphenyl)carbamic acid tert-butyl ester (30 g, 0.091 mol) and 4-chlorophenylboronic acid (21.54 g, 0.138 mol) in acetone (3000 ml), and the mixture is stirred at room temperature under an atmosphere of nitrogen. Palladium acetate (1.02 g, 0.004 mol) and 2-(dicyclohexylphosphino)-2′,4′,6′-tri-iso-propyl-1,1′-biphenyl (4.33 g, 0.009 mol) are added and the reaction mixture is stirred at room temperature for 12 hours. The mixture is filtered through diatomaceous earth, and the filtrate is evaporated under reduced pressure to remove most of the acetone. The remaining solution is extracted with ethyl acetate (3×300 ml). The organic extracts are combined and concentrated under reduced pressure to give (4′-chloro-3,5-diethylbiphen-4-yl)carbamic acid tent-butyl ester (22 g).

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 12 hours
  2. filtrationThe mixture is filtered through diatomaceous earth
  3. customthe filtrate is evaporated under reduced pressure
  4. customto remove most of the acetone
  5. extractionThe remaining solution is extracted with ethyl acetate (3×300 ml)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c1bb3f67251942fa98fc66ac298dccf8
Source dataset
uspto-grants-2014_11
Patent number
US08895761B2

Reaction notes

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