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Water → Ethyl 2-(2-(3-aminophenyl)-5-(1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-3-fluoro-2-phenyl-1H-indole-6-carbonyl)thiophen-3-yl)acetate

HRID 1952511
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1952511
Br[C:2]1[S:3][C:4]([C:13]([C:15]2[CH:23]=[C:22]3[C:18]([C:19]([F:45])=[C:20]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[N:21]3[CH2:24][CH2:25][CH2:26][CH2:27][N:28]3[C:36](=[O:37])[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:29]3=[O:38])=[CH:17][CH:16]=2)=[O:14])=[CH:5][C:6]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[F-].[Cs+].[NH2:48][C:49]1[CH:50]=[C:51](B(O)O)[CH:52]=[CH:53][CH:54]=1.O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:48][C:49]1[CH:54]=[C:53]([C:2]2[S:3][C:4]([C:13]([C:15]3[CH:23]=[C:22]4[C:18]([C:19]([F:45])=[C:20]([C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)[N:21]4[CH2:24][CH2:25][CH2:26][CH2:27][N:28]4[C:36](=[O:37])[C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[C:29]4=[O:38])=[CH:17][CH:16]=3)=[O:14])=[CH:5][C:6]=2[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:52]=[CH:51][CH:50]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 25953Cesium fluorideHCID 922693-Aminophenylboronic acidHCID 67496700Ethyl 2-(2-bromo-5-(1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-3-fluoro-2-phenyl-1H-indole-6-carbonyl)thiophen-3-yl)acetate

Produkt 1

HCID 67496828Ethyl 2-(2-(3-aminophenyl)-5-(1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-3-fluoro-2-phenyl-1H-indole-6-carbonyl)thiophen-3-yl)acetate
Ausbeute 76,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of 6 (40 mg, 0.058 mmol), Pd(PPh3)4 (13 mg, 0.011 mmol), CsF (27 mg, 0.18 mmol), 3-aminophenylboronic acid (12 mg, 0.088 mmol), and H2O (80 μL) in DME (8 mL) was degassed with N2 for 10 minutes and then refluxed. When the reaction was over by TLC monitoring, the mixture was poured into H2O (10 mL) and then extracted with 70 mL Et2O. The organic layer was washed with brine (2×10 mL), dried over MgSO4, and then concentrated in vacuo. MPLC purification (Hex:EtOAc/5:1) of the residue gave 7 as a yellow amorphous solid (31 mg, 76%). 1H NMR (400 MHz, CDCl3) δ 8.00 (s, 1H), 7.78-7.67 (m, 7H), 7.51-7.41 (m, 5H), 7.23 (t, J=8.0 Hz, 1H), 6.90 (d, J=7.6 Hz, 1H), 6.85 (s, 1H), 6.73 (d, J=8.0 Hz, 1H), 4.26 (t, J=7.0 Hz, 2H), 4.15 (q, J=7.2 Hz, 2H), 3.82 (brs, 2H), 3.70 (s, 2H), 3.48 (t, J=6.8 Hz, 2H), 1.66-1.60 (m, 2H), 1.48-1.45 (m, 2H), and 1.25 (t, J=7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 188.13, 171.26, 168.49, 149.66, 147.09, 143.16, 141.68, 140.71, 137.58, 134.19, 132.51, 132.44, 132.38, 132.14, 130.54, 130.05, 129.97, 129.54, 129.15, 129.06, 128.94, 128.58, 127.31, 127.10, 123.47, 121.43, 120.02, 119.86, 119.71, 116.81, 115.88, 115.69, 112.56, 61.31, 43.61, 37.25, 34.77, 27.36, 25.77, and 14.45; 19F NMR (376 MHZ, CDCl3) δ −174.49.

Aufarbeitung

  1. customwas degassed with N2 for 10 minutes
  2. temperaturerefluxed
  3. additionthe mixture was poured into H2O (10 mL)
  4. extractionextracted with 70 mL Et2O
  5. washThe organic layer was washed with brine (2×10 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customMPLC purification (Hex:EtOAc/5:1) of the residue

Quellen und Nachweise

ORD-Eintrag
ord-b00440db0abe4f51b41b0b1930a692dd
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08404728B2

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