Ammonium Chloride → HCID 136166849, compound

HRID 1617467Notes

Reaction equation

HRID 1617467 reaction equation
C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.Br[C:23]1[CH:28]=[CH:27][C:26]([CH:29]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[CH3:46])[CH2:30][C:31]([C:34]2[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=2)=[N:32][OH:33])=[CH:25][CH:24]=1.[CH3:47][O:48][CH2:49][CH2:50][NH:51][CH3:52].[NH4+].[Cl-]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:47][O:48][CH2:49][CH2:50][N:51]([CH3:52])[C:23]1[CH:28]=[CH:27][C:26]([CH:29]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[CH3:46])[CH2:30]/[C:31](/[C:34]2[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=2)=[N:32]\[OH:33])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 300977(2-Methoxyethyl)(methyl)amineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 136359968HCID 136359968, compound

Product 1

HCID 136166849HCID 136166849, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a suspension of tris(dibenzylideneacetone)dipalladium (23 mg), sodium tert-butylate (83 mg), 2(di-tertbutylphosphino)biphenyl (15 mg) and 3-(4-bromo-phenyl)-1-pyridin-4-yl-3-o-tolyl-propan-1-one oxime (example 31, 200 mg) in toluene (10 mL) was added a solution of N (2-methoxyethyl)methylamine (158 mg) in toluene (10 mL). The reaction mixture was stirred at 80° C. overnight, cooled to room temperature and a saturated aqueous solution of NH4Cl was added. The phases were separated and the inorganic layer was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Column chromatography on silica gel (EtOAc/n-heptane 2:1 to EtOAc) yielded (E)-3-{4-[(2-methoxy-ethyl)-methyl-amino]-phenyl}-1-pyridin-4-yl-3-o-tolyl-propan-1-one oxime containing less than 10% of the Z isomer (88 mg, 43%) as a yellow foam, MS (ESI+): m/z=404.3 ([M+H]+).

Workup

  1. temperaturecooled to room temperature
  2. customThe phases were separated
  3. extractionthe inorganic layer was extracted with EtOAc (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ffdefdcad7d648afa676349f5d60d724
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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