Nitrogen → HCID 131730651, compound

HRID 1257913Notes

Reaction equation

HRID 1257913 reaction equation
F[B-](F)(F)F.[C:6]([PH+](C(C)(C)C)C(C)(C)C)(C)(C)[CH3:7].N#N.Br[C:22]1[CH:23]=[C:24]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])(C)C)[CH:25]=[CH:26][CH:27]=1.[CH2:36]([OH:39])[CH:37]=[CH2:38].C1(N(C)C2CCCCC2)CCCCC1>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].O1CCOCC1>[CH2:31]([O:30][C:29](=[O:35])[NH:28][C:24]1[CH:25]=[CH:26][CH:27]=[C:22]([CH2:38][CH2:37][CH:36]=[O:39])[CH:23]=1)[CH2:34][CH2:6][CH3:7]

Participants

8

Reactant 5

HCID 947NitrogenHCID 7858Allyl AlcoholHCID 24210N-Methyl dicyclohexylamineHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 2757254N-(tert-Butoxycarbonyl)-3-bromoaniline

Product 1

HCID 131730651HCID 131730651, compoundYield 911.6%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

Tris(dibenzylideneacetone)dipalladium (0.10 g, 0.00011 mol) and tri-tert-butylphosphonium tetrafluoroborate (0.064 g, 0.00022 mol) in a flask was evacuated and refilled with N2 (3 times). Then 1,4-dioxane (7.0 mL) was added followed by consecutive addition of tert-butyl (3-bromophenyl)carbamate (2.00 g, 0.00735 mol), 2-propen-1-ol (0.854 g, 0.0147 mol), N-cyclohexyl-N-methyl-cyclohexanamine (1.7 g, 0.0088 mol). The reaction mixture was stirred at 40° C. overnight, filtered, and washed with dichloromethane. The filtrate was concentrated and purified by chromatography on silica gel with 40% EtOAc in hexanes to afford the desired product (0.5 g, 30%).

Workup

  1. filtrationfiltered
  2. washwashed with dichloromethane
  3. concentrationThe filtrate was concentrated
  4. custompurified by chromatography on silica gel with 40% EtOAc in hexanes

Sources & evidence

ORD record
ord-075f8a4ab782479b8ae393550cddf940
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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