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Triphenylphosphine → HCID 59321567、化合物

HRID 2423524
ノート
印刷プレビュー

反応式

HRID 2423524 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 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

生成物 1

HCID 59321567HCID 59321567、化合物収率 52%

試薬・触媒・溶媒

4
HCID 167845palladium(II) acetate触媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
60 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-54cfc9d5583043ccabc7f771a269d715
出典データセット
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07960552B2

反応ノート

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