Acetonitrile → HCID 20347035, compound

HRID 1922559Notes

Reaction equation

HRID 1922559 reaction equation
[CH:1]([C:5]1[CH:11]=[CH:10][CH:9]=[C:8](Br)[C:6]=1[NH2:7])([CH2:3][CH3:4])[CH3:2].[C:13](B1OC(C)(C)C(C)(C)O1)([CH3:15])=[CH2:14].CC#N.C([O-])([O-])=O.[K+].[K+]>O.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>[CH:1]([C:5]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:13]([CH3:15])[CH3:14])[C:6]=1[NH2:7])([CH2:3][CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 59509800HCID 59509800, compound

Product 1

HCID 20347035HCID 20347035, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

(−)-2-Sec-butyl-6-bromoaniline (2) (0.684 g, 3 mmol), isopropenylboronic acid pinacol ester (1 g, 6 mmol), tetrakis(triphenylphosphine)palladium(0) (0.035 g, 0.03 mmol), MeCN 10 ml and K2CO3 (5 ml, 1M solution) were heated in a microwave at 160° C. for 400 sec. The reaction mixture was diluted with water (75 ml). Products were extracted with ethyl acetate (50 ml). The organic layer was washed with 5% NaHCO3, brine and dried over anhydrous MgSO4. The solvent was removed under reduced pressure, and the compound purified by silica gel chromatography (CombiFlash, 30 g column, hexane-ethyl acetate). The reduction was then performed in MeOH (40 ml) over 5% Pd/C (˜0.3 g), hydrogen pressure 60 psi overnight (0.48 g, 72%).

Workup

  1. extractionProducts were extracted with ethyl acetate (50 ml)
  2. washThe organic layer was washed with 5% NaHCO3, brine
  3. dry with materialdried over anhydrous MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customthe compound purified by silica gel chromatography (CombiFlash, 30 g column, hexane-ethyl acetate)
  6. customwas then performed in MeOH (40 ml) over 5% Pd/C (˜0.3 g), hydrogen pressure 60 psi overnight (0.48 g, 72%)

Sources & evidence

ORD record
ord-4134fc936c984028a1428001499c65c2
Source dataset
uspto-grants-2012_05
Patent number
US08173849B2

Reaction notes

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