Triethylamine → 3-Cyclopropyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-benzisoxazole

HRID 593731Notes

Reaction equation

HRID 593731 reaction equation
C1(P(C2CCCCC2)C2C=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[C:19]([O:20]C)=[CH:18][CH:17]=[CH:16][C:15]=2OC)CCCCC1.C([N:32](CC)CC)C.[CH3:37][C:38]1([CH3:45])[C:42]([CH3:44])([CH3:43])[O:41][BH:40][O:39]1>CC#N.CC#N.Cl[Pd]Cl>[CH:10]1([C:9]2[C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([B:40]4[O:41][C:42]([CH3:44])([CH3:43])[C:38]([CH3:45])([CH3:37])[O:39]4)[C:19]=3[O:20][N:32]=2)[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 867303943-Cyclopropyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-benzisoxazole

Reagents, catalysts & solvents 1

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalyst

Conditions

Temperature
110 °C

Procedure

A vial was charged with bis(acetonitrile)palladium(II) chloride (1.090 mg, 4.20 μmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (3.45 mg, 8.40 μmol), and Preparation 28D (0.050 g, 0.210 mmol). The vial was capped with a rubber septum and then evacuated and backfilled with N2 (this sequence was carried out a total of 2 times). Dioxane (0.126 mL) was added via syringe, through the septum, followed by the addition of triethylamine (0.088 mL, 0.630 mmol) and 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.046 mL, 0.315 mmol). The septum was then replaced with a Teflon screw valve, and the vial sealed. The reaction mixture was heated at 110° C. After 19 hr, the reaction mixture was allowed to cool to room temperature. The reaction mixture was filtered through a disposable fritted funnel and the filter cake washed with CH2Cl2. The filtrate was concentrated to afford the title compound as a brown residue (60 mg, 100%).

Workup

  1. customThe vial was capped with a rubber septum
  2. customevacuated
  3. additionDioxane (0.126 mL) was added via syringe, through the septum
  4. temperatureto cool to room temperature
  5. filtrationThe reaction mixture was filtered through a disposable fritted funnel
  6. washthe filter cake washed with CH2Cl2
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-77e2d700e979453f9ce80ef40bd35e8d
Source dataset
uspto-grants-2016_01
Patent number
US09242967B2

Reaction notes

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