1,4-Dioxane → (S)-N-(2-hydroxy-1-phenylethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

HRID 595789Notes

Reaction equation

HRID 595789 reaction equation
Br[C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][C@@H:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][OH:11])=[O:7])=[CH:4][CH:3]=1.[O:20]1CCO[BH:21]1.[CH:25]1(P(C2CCCCC2)C2CCCCC2)[CH2:30]CCC[CH2:26]1.[C:44]([O-:47])(=O)[CH3:45].[K+].O1CCOC[CH2:50]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:11][CH2:10][C@@H:9]([NH:8][C:6](=[O:7])[C:5]1[CH:18]=[CH:19][C:2]([B:21]2[O:20][C:25]([CH3:30])([CH3:26])[C:44]([CH3:45])([CH3:50])[O:47]2)=[CH:3][CH:4]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 312751,4-DioxaneHCID 75806TricyclohexylphosphineHCID 517044Potassium AcetateHCID 5326306InChI=1/C2H5BO2/c1-2-5-3-4-1/h3H,1-2HHCID 113356449(S)-4-bromo-N-(2-hydroxy-1-phenylethyl)benzamide

Product 1

HCID 123160895(S)-N-(2-hydroxy-1-phenylethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
100 °C

Procedure

To a solution of (S)-4-bromo-N-(2-hydroxy-1-phenylethyl)benzamide, 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane (B2(PlN)2) (238 mg, 0.937 mmol), Pd2(dba)3 (21.45 mg, 0.023 mmol), tricyclohexylphosphine (19.71 mg, 0.070 mmol) in dioxane (1.562 mL) was added potassium acetate (138 mg, 1.405 mmol). The reaction mixture was degassed by N2 stream for 15 min. The reaction mixture was heated at 100° C. overnight. After diluted with EtOAc, the reaction mixture was filtered through Celite. After concentrated, (S)—N-(2-hydroxy-1-phenylethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide was used for the next step without further purification. LCMS (m/z): 368.3 (MH+), 0.88 min (for boronic ester) and 286.1 (MH+), 0.49 min (for the corresponding boronic acid).

Workup

  1. customThe reaction mixture was degassed by N2 stream for 15 min
  2. additionAfter diluted with EtOAc
  3. filtrationthe reaction mixture was filtered through Celite
  4. concentrationAfter concentrated
  5. custom(S)—N-(2-hydroxy-1-phenylethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide was used for the next step without further purification
  6. custom368.3 (MH+), 0.88 min (for boronic ester) and 286.1 (MH+), 0.49 min

Sources & evidence

ORD record
ord-6098c9e485cb494493c2af9a6a9a169a
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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