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

HRID 595789노트

반응식

HRID 595789 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

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온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6098c9e485cb494493c2af9a6a9a169a
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242996B2

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