Cesium carbonate → 3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-({[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxy}methyl)isoxazole

HRID 2423520Notes

Reaction equation

HRID 2423520 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][C:8]1([CH3:22])[C:12]([CH3:14])([CH3:13])[O:11][B:10]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[O:9]1.Cl[CH2:24][C:25]1[C:26]([C:33]2[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][C:34]=2[Cl:40])=[N:27][O:28][C:29]=1[CH:30]([CH3:32])[CH3:31]>CN(C)C=O>[Cl:39][C:38]1[CH:37]=[CH:36][CH:35]=[C:34]([Cl:40])[C:33]=1[C:26]1[C:25]([CH2:24][O:21][C:18]2[CH:19]=[CH:20][C:15]([B:10]3[O:9][C:8]([CH3:22])([CH3:7])[C:12]([CH3:13])([CH3:14])[O:11]3)=[CH:16][CH:17]=2)=[C:29]([CH:30]([CH3:32])[CH3:31])[O:28][N:27]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 592648754-(Chloromethyl)-3-(2,6-dichlorophenyl)-5-isopropylisoxazole

Product 1

HCID 597090393-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-({[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxy}methyl)isoxazoleYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Cesium carbonate (1.96 g, 6.03 mmol) was added to 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol (1.26 g, 5.74 mmol) and 4-(chloromethyl)-3-(2,6-dichlorophenyl)-5-(1-methylethyl)isoxazole (1.75 g, 5.74 mmol) in N,N-dimethylformamide (57 mL) at room temperature. The resulting suspension was heated for sixty-nine hours at 60° C. The reaction was cooled and concentrated to remove the N,N-dimethylformamide, then water was added and the reaction mixture was extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was purified by silica gel chromatography eluting with 1:6 ethyl acetate:hexanes to give 2.24 g (80%) of 3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-({[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxy}methyl)isoxazole as an solid. 1H NMR (400 MHz, d6-DMSO): δ 7.62-7.59 (m, 2H), 7.55-7.48 (m, 3H), 6.76 (d, J=9 Hz, 2H), 4.82 (s, 2H), 3.44 (septet, J=7 Hz, 1H), 1.31 (d, J=7 Hz, 6H), 1.24 (s, 12H). ESI-LCMS m/z 488 (M+H)+.

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. customto remove the N,N-dimethylformamide
  4. additionwater was added
  5. extractionthe reaction mixture was extracted with diethyl ether
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with 1:6 ethyl acetate

Sources & evidence

ORD record
ord-86d8b31279e8427da327036d926fa1a5
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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