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Triphenylphosphine → HCID 59321567, 화합물

HRID 2423524
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HRID 2423524 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:5]2.[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:20]=1[C:26]1[C:30]([CH2:31][O:32][C:33]2[CH:38]=[CH:37][C:36](B3OC(C)(C)C(C)(C)O3)=[CH:35][CH:34]=2)=[C:29]([CH:48]([CH3:50])[CH3:49])[O:28][N:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O.O1CCOCC1>[Cl:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([Cl:18])[C:20]=1[C:26]1[C:30]([CH2:31][O:32][C:33]2[CH:34]=[CH:35][C:36]([C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[N:8]=[C:7]([CH3:12])[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:5]4)=[CH:37][CH:38]=2)=[C:29]([CH:48]([CH3:50])[CH3:49])[O:28][N:27]=1
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참가 물질

9

반응물 4

HCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 17039982Ethyl 6-bromo-2-methylquinoline-3-carboxylateHCID 597090393-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-({[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxy}methyl)isoxazole

생성물 1

HCID 59321567HCID 59321567, 화합물수율 52%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매2회HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
60 °C

실험 절차

Palladium(II)acetate (1.2 mg, 5.3 μmol) was added to ethyl 6-bromo-2-methyl-3-quinolinecarboxylate (31.0 mg, 105.5 μmol), 3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-({[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxy}methyl)isoxazole (51.5 mg, 105.5 μmol), triphenylphosphine (2.7 mg, 10.5 μmol), and potassium phosphate (78.3 mg, 369.2 μmol). Then, dioxane (2.1 mL) was added to the mixture, followed by water (10.5 μL), and the reaction mixture was heated open to the atmosphere at 60° C. in an oil bath for 21 hours, then allowed to cool to room temperature. Water was added, followed by ethyl acetate, and the mixture was filtered through Celite®. The filtrate was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was purified by silica gel chromatography eluting with 3:7 ethyl acetate:hexanes to give 31.6 mg (52%) of ethyl 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-methyl-3-quinolinecarboxylate as a solid. 1H NMR (400 MHz, d6-DMSO): δ 8.87 (s, 1H), 8.32 (d, J=2 Hz, 1H), 8.11 (dd, J=9, 2 Hz, 1H), 7.99 (d, J=9 Hz, 1H), 7.70 (d, J=9 Hz, 2H), 7.66-7.60 (m, 2H), 7.55 (dd, J=9, 7 Hz, 1H), 6.93 (d, J=9 Hz, 2H), 4.88 (s, 2H), 4.38 (q, J=7 Hz, 2H), 3.48 (septet, J=7 Hz, 1H), 2.85 (s, 3H), 1.38 (t, J=7 Hz, 3H), 1.34 (d, J=7 Hz, 6H). ESI-LCMS m/z 575 (M+H)+.

후처리

  1. temperatureto cool to room temperature
  2. filtrationthe mixture was filtered through Celite®
  3. extractionThe filtrate was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 3:7 ethyl acetate

출처 및 근거

ORD 기록
ord-54cfc9d5583043ccabc7f771a269d715
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07960552B2

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