Cesium fluoride → HCID 69202470, compound

HRID 2220661Notes

Reaction equation

HRID 2220661 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[F-].[Cs+].BrC1C=CC(OC[CH2:21][NH:22][CH2:23][C@@H:24]([C:26]2[CH:27]=[CH:28][C:29]([O:46][CH2:47][O:48][CH2:49][CH2:50][Si:51]([CH3:54])([CH3:53])[CH3:52])=[C:30]([N:32](OCOCC[Si](C)(C)C)[S:33]([CH3:36])(=[O:35])=[O:34])[CH:31]=2)[OH:25])=CC=1>C(O)C.O1CCOCC1.O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:25][C@H:24]([C:26]1[CH:27]=[CH:28][C:29]([O:46][CH2:47][O:48][CH2:49][CH2:50][Si:51]([CH3:52])([CH3:53])[CH3:54])=[C:30]([N:32]([CH2:47][O:48][CH2:49][CH2:50][Si:51]([CH3:54])([CH3:53])[CH3:52])[S:33]([CH3:36])(=[O:34])=[O:35])[CH:31]=1)[CH2:23][NH:22][CH2:21][CH2:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:5][CH:4]=1

Participants

8

Reactant 3

HCID 25953Cesium fluorideHCID 201262(4-Methoxyphenyl)boronic acidHCID 86611777HCID 86611777, compound

Product 1

HCID 69202470HCID 69202470, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 4-methoxyphenylboronic acid (0.013 g) in ethanol (0.06 mL), an aqueous solution (0.10 mL) of cesium fluoride (0.019 g) and a solution of tetrakis(triphenylphosphine)palladium (0.003 g) in 1,4-dioxane (0.10 mL) were added successively to a solution of N-[5-{(R)-2-[2-(4-bromophenoxy)-ethylamino]-1-hydroxyethyl}-2-(2-trimethylsilylethoxymethoxy)phenyl]-N-(2-trimethylsilylethoxymethoxy)methanesulfonamide (0.03 g) in 1,4-dioxane (0.20 mL), and the mixture was stirred at 100° C. for 12 hrs. After being cooled to room temperature, the reaction mixture was diluted with tetrahydrofuran, and purified by SCX ion exchange column chromatography (Varian Bond Elut 500 mg, preconditioning: tetrahydrofuran, washing solvent: tetrahydrofuran, eluent: 2 mol/L ammonia in methanol). The solvent was evaporated under reduced pressure to afford N-[5-{(R)-1-hydroxy-2-[2-(4′-methoxybiphenyl-4-yloxy)ethylamino]ethyl}-2-(2-trimethylsilylethoxymethoxy)phenyl]-N-(2-trimethylsilylethoxymethyl)methanesulfonamide.

Workup

  1. temperatureAfter being cooled to room temperature
  2. custompurified by SCX ion exchange column chromatography (Varian Bond Elut 500 mg, preconditioning: tetrahydrofuran, washing solvent: tetrahydrofuran, eluent: 2 mol/L ammonia in methanol)
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-753f9c9160044a4b97b97fdc7d3ffc00
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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