Potassium Acetate → 1-(4-(2-Hydroxy-2-methylpropoxy)-3-methoxyphenyl)-2-oxo-1,2-dihydropyridin-4-ylboronic acid

HRID 1044410

반응식

HRID 1044410 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])=[C:10]([O:20][CH3:21])[CH:9]=2)[C:4](=[O:22])[CH:3]=1.CC1(C)C(C)(C)[O:27][B:26](B2OC(C)(C)C(C)(C)O2)[O:25]1.C([O-])(=O)C.[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>O1CCOCC1.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.C(Cl)(Cl)Cl.[Pd].[Pd]>[OH:19][C:16]([CH3:18])([CH3:17])[CH2:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([N:5]2[CH:6]=[CH:7][C:2]([B:26]([OH:27])[OH:25])=[CH:3][C:4]2=[O:22])=[CH:9][C:10]=1[O:20][CH3:21]

참가 물질

7

반응물 4

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 585802944-chloro-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyridin-2(1H)-one

생성물 1

HCID 585802101-(4-(2-Hydroxy-2-methylpropoxy)-3-methoxyphenyl)-2-oxo-1,2-dihydropyridin-4-ylboronic acid수율 36.3%

시약·촉매·용매 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)촉매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 4-chloro-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyridin-2(1H)-one Part D of procedure 9 (300 mg, 0.93 mmol), 4,4,4′, 4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (706 mg, 2.78 mmol), potassium acetate (273 mg, 2.78 mmol), TRIS(DIBENZYLIDENEACETONE)-DIPALLADIUM(0)-CHLOROFORM ADDUCT (67 mg, 0.06 mmol), and X-Phos (133 mg, 0.28 mmol) in Dioxane (6 mL) was stirred at 90° C. for 18 hours (Mullen et al, JOC, 2008, 73 (23) 9207-9213). The reaction was filtered and concentrated. The crude was purified using ISCO flash chromatography (silica gel/methylene chloride/methanol 100:0 to 90:10 gradient) to afford the desired product 1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)-2-oxo-1,2-dihydropyridin-4-ylboronic acid 12A (112 mg, 0.336 minol, 36.3% yield) as a brown solid. LC/MS 334 (M+H)+, tR 0.59 min (method 5)

후처리

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. customThe crude was purified

출처 및 근거

ORD 기록
ord-8eb931179ec64d0ca10fbbba76dbb56d
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563583B2

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