Triethylamine → HCID 67817705, compound

HRID 2401334Notes

Reaction equation

HRID 2401334 reaction equation
CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[C:35]([O:43][CH2:44][C:45]1[O:49][N:48]=[C:47]([CH3:50])[C:46]=1Br)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.CCN(CC)CC.[CH3:59][C:60]1([CH3:67])[C:64]([CH3:66])([CH3:65])[O:63][BH:62][O:61]1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:35]([O:43][CH2:44][C:45]1[O:49][N:48]=[C:47]([CH3:50])[C:46]=1[B:62]1[O:63][C:64]([CH3:66])([CH3:65])[C:60]([CH3:67])([CH3:59])[O:61]1)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 67814058HCID 67814058, compound

Product 1

HCID 67817705HCID 67817705, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a resealable vial was added Pd(OAc)2 (3.87 mg, 0.017 mmol) and X-phos (16.42 mg, 0.034 mmol) before the vial was sealed and evacuated and purged with N2 (3×). To this vial was added (4-bromo-3-methylisoxazol-5-yl)methyl benzoate (102 mg, 0.344 mmol) in dioxane (1 mL), Et3N (144 μl, 1.033 mmol), and 4,4,5,5-tetramethyl-1,3,2-dioxaborolane solution (517 μl, 1M in THF, 0.517 mmol). The reaction was stirred overnight at 80° C., cooled to room temperature and filtered. The filtrate was concentrated to afford crude (3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazol-5-yl)methyl benzoate. To a resealable vial was added K2CO3 (47.5 mg, 0.344 mmol), PdCl2(dppf)-CH2Cl2 Adduct (20.06 mg, 0.025 mmol), (2-bromophenyl)(4-chlorophenyl)methanone (72.6 mg, 0.246 mmol). The vial was sealed and evacuated and purged with N2 (3×) before addition of crude (3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazol-5-yl)methyl benzoate (118 mg, 0.344 mmol) dissolved in dioxane (2 mL). Water (0.5 mL) was then added to this solution before the vial was heated to 110° C. overnight. The reaction was cooled to room temperature, diluted with EtOAc, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford (4-(2-(4-chlorobenzoyl)phenyl)-3-methylisoxazol-5-yl)methyl benzoate. LC/MS m/z 432 [M+H]+.

Workup

  1. customwas sealed
  2. customevacuated
  3. custompurged with N2 (3×)
  4. temperaturecooled to room temperature
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-30d1b9a2ac6e4b93bf306d5b784af2d8
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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