Cesium carbonate → 5'-tert-Butoxycarbonylamino-2'-trifluoromethoxy-biphenyl-4-carboxylic acid ethyl ester

HRID 1678476Notes

Reaction equation

HRID 1678476 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[C:10](Br)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:21]([O:23][C:24]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)=[O:25])[CH3:22].C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC>[CH2:21]([O:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([C:10]2[CH:9]=[C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:20])[CH:13]=[CH:12][C:11]=2[O:14][C:15]([F:18])([F:17])[F:16])=[CH:28][CH:27]=1)=[O:25])[CH3:22]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27343504-Ethoxycarbonylphenylboronic acidHCID 59822358(3-Bromo-4-trifluoromethoxy-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 598223825'-tert-Butoxycarbonylamino-2'-trifluoromethoxy-biphenyl-4-carboxylic acid ethyl esterYield 72.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of (3-bromo-4-trifluoromethoxy-phenyl)-carbamic acid tert-butyl ester (250 mg), 4-ethoxycarbonyl-phenyl boronic acid (136 mg), cesium carbonate (228 mg) and tetrakis(triphenylphosphine)palladium0 (catalytic quantity), in 1:2 aqueous DME (15 ml) was heated to reflux for 18 h. The mixture was then cooled and partitioned between water and ethyl acetate. The dried extracts were evaporated and the residue purified on silica gel. Elution with 5-40% ethyl acetate:petrol gave a pale yellow solid (217 mg)

Workup

  1. temperatureto reflux for 18 h
  2. temperatureThe mixture was then cooled
  3. custompartitioned between water and ethyl acetate
  4. customThe dried extracts were evaporated
  5. customthe residue purified on silica gel
  6. washElution with 5-40% ethyl acetate

Sources & evidence

ORD record
ord-85c230e72c5d4aa19212fe0cb61dab78
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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