Cesium fluoride → HCID 131721884, compound

HRID 2288932Notes

Reaction equation

HRID 2288932 reaction equation
[CH3:1][N:2]([CH2:11][C:12]1[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=1)[S:3]([CH2:6][C:7]([O:9][CH3:10])=[O:8])(=[O:5])=[O:4].[C:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)#[N:20].[F-].[Cs+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(COC)OC.ClCCl>[CH3:10][O:9][C:7](=[O:8])[CH2:6][S:3]([N:2]([CH3:1])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:24]2[CH:25]=[CH:26][C:21]([C:19]#[N:20])=[CH:22][CH:23]=2)=[CH:14][CH:13]=1)(=[O:5])=[O:4]

Participants

7

Reactant 4

HCID 25953Cesium fluorideHCID 80271Tri-o-tolylphosphineHCID 27343264-Cyanophenylboronic acidHCID 18702043HCID 18702043, compound

Product 1

HCID 131721884HCID 131721884, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of methyl 2-({methyl[(4-bromophenyl)methyl]amino}sulfonyl)acetate (300 mg, 0.9 mmol) in dimethoxyethane (5 ml) was added 4-cyanophenylboronic acid (Preparation 6, 150 mg, 1.0 mmol), caesium fluoride (290 mg), tri-ortho-tolyl phosphine (28 mg, 0.09 mmol) and bis(benzylideneacetone)palladium(0) (25 mg, 0.04 mmol) and the mixture was heated to reflux for 1 hour under an atmosphere of nitrogen. The mixture was cooled to ambient temperature, diluted with dichloromethane (30 ml) and washed with water. The organic layer was dried (Na2SO4), the solvent was evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel (hexane/ethyl acetate 2:1 as eluent) to give the titled compound as a pale yellow low melting solid (230 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour under an atmosphere of nitrogen
  3. washwashed with water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified by flash chromatography on silica gel (hexane/ethyl acetate 2:1 as eluent)

Sources & evidence

ORD record
ord-bfe1078f97f940d19d3452da8bef8573
Source dataset
uspto-grants-2000_07
Patent number
US06090852

Reaction notes

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