Sodium Carbonate → HCID 9902862, compound

HRID 1072655Notes

Reaction equation

HRID 1072655 reaction equation
Br[C:2]1[CH:18]=[CH:17][C:5]([O:6][CH:7]([CH3:16])[CH2:8][NH:9][S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[CH:4][CH:3]=1.[CH3:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.O1CCOCC1>[CH3:14][CH:13]([S:10]([NH:9][CH2:8][CH:7]([O:6][C:5]1[CH:17]=[CH:18][C:2]([C:24]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:19])[CH:25]=2)=[CH:3][CH:4]=1)[CH3:16])(=[O:12])=[O:11])[CH3:15]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27339503-Tolylboronic acidHCID 9840705HCID 9840705, compound

Product 1

HCID 9902862HCID 9902862, compoundYield 6.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

The title compound (18 mg, 6%, white foam) was prepared from [2-(4-bromophenoxy)propyl][(methylethyl)sulfonyl]amine (275 mg, 0.818 mmol, prepared in example 1), 3-methylbenzeneboronic acid (135 mg, 0.993 mmol), tetrakis(triphenylphosphine)palladium(0) (15 mg, 0.013 mmol), 2 M sodium carbonate (295 mg in 1.4 mL water) and 1,4-dioxane (5.5 mL) was prepared in a manner analogous to the procedure described in Example 2. The crude material was purified utilizing a Chromatotron® with a 2000 μm rotor in a 1:1 hexane:ethyl acetate solvent system, yielding 110 mg of a co-eluting mixture of unreacted starting material and title compound. This mixture was further purified by reverse phase, chromatography on a Vydac C-18 column in a gradient of 5 to 70% of 0.1% trifluoroacetic acidlacetonitrile in water over 45 minutes at 200 mL/min elution rate.

Workup

  1. customwas prepared in a manner analogous to the procedure
  2. customThe crude material was purified

Sources & evidence

ORD record
ord-5550a822d3fa4caa989a34f00ea26d3f
Source dataset
uspto-grants-2005_06
Patent number
US06911476B2

Reaction notes

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