Tert-Butylamine → HCID 68675657, compound

HRID 2089717Notes

Reaction equation

HRID 2089717 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4](I)[CH:3]=1.[CH:10]1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[CH3:29][C:30]([O:35][CH2:36][C:37]#[CH:38])([CH3:34])[C:31]([OH:33])=[O:32].C(N)(C)(C)C>O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:10][O:32][C:31](=[O:33])[C:30]([O:35][CH2:36][C:37]#[C:38][C:4]1[CH:3]=[C:2]([Cl:1])[CH:8]=[CH:7][C:5]=1[NH2:6])([CH3:34])[CH3:29]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 75806TricyclohexylphosphineHCID 27576154-Chloro-2-iodoanilineHCID 55303306HCID 55303306, compound

Product 1

HCID 68675657HCID 68675657, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 2 g (7.89 mM) of 4-chloro-2-iodoaniline, 75 mg (0.395 mM) of cuprous iodide, 277 mg (0.39 mM) of bis(triphenylphosphine)dichloropalladium, 221 mg (0.79 mM) of tri-(cyclohexyl)phosphine, 3.08 g (19.7 mM) of the methyl ester of 2-methyl-2-(2-propynyloxy)-propanoic acid and 15 ml of tert-butylamine is prepared. The reaction mixture is refluxed gently for 16 hours and then cooled, hydrolyzed in 60 ml of water and extracted with 3×40 ml of dichloromethane. The combined organic phases are washed with water and then dried over magnesium sulfate and concentrated under reduced pressure. The residual oil is purified by chromatography on silica gel using a dichloromethane/ethyl acetate mixture (98/2; v/v) as the eluent to give 1.84 g of the expected product in the form of an orange oil (yield=83%).

Workup

  1. customis prepared
  2. temperatureThe reaction mixture is refluxed gently for 16 hours
  3. extractionextracted with 3×40 ml of dichloromethane
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residual oil is purified by chromatography on silica gel using a dichloromethane/ethyl acetate mixture (98/2; v/v) as the eluent

Sources & evidence

ORD record
ord-572797178eba46e19260fe39fbbd69db
Source dataset
uspto-grants-2013_05
Patent number
US08436040B2

Reaction notes

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