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Cesium carbonate → HCID 86729626, Verbindung

HRID 2284900
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2284900
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:16](=[O:19])[CH:17]=[CH2:18])[C:5]([Cl:20])=[CH:4][N:3]=1.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]([CH2:32][CH3:33])[C:29](=[O:31])[CH3:30])=[CH:24][C:23]=1[C:34]([F:37])([F:36])[F:35].C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:20][C:5]1[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:16](=[O:19])[CH:17]=[CH2:18])=[N:7][C:2]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]([CH2:32][CH3:33])[C:29](=[O:31])[CH3:30])=[CH:24][C:23]=2[C:34]([F:35])([F:36])[F:37])=[N:3][CH:4]=1
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Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86729624HCID 86729624, VerbindungHCID 86729627HCID 86729627, Verbindung

Produkt 1

HCID 86729626HCID 86729626, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845
palladium(II) acetate
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of Intermediate 1 from Example 162 (100 mg, 0.3246 mmol) in tetrahydrofuran (5 mL), N-(4-amino-3-(trifluoro methyl)phenyl)-N-ethylacetamide (80 mg, 0.3246 mmol) and cesium carbonate (316 mg, 0.9738 mmol) were added and degassed for 10 min. To the reaction mixture palladium acetate (38 mg, 0.1623 mmol) and xanthphos (36.8 mg, 0.0973 mmol) were added and again degassed for another 5 min. The mixture was irradiated by microwave at 80° C. for 20 min. TLC showed completion of starting material (TLC system: 10% methanol/chloroform, (Rf): 0.5). The reaction was quenched with water (15 mL) and extracted with ethyl acetate (3×10 mL). The organic layer was separated, dried over sodium sulfate and concentrated. The crude compound was purified by prep-HPLC to obtain the title compound as yellow solid. (30 mg, 17%). 1HNMR (DMSO-d6) δ 0.98 (m, 3H), 1.70 (m, 3H), 1.85 (s, 1H), 3.63 (m, 2H), 5.77-5.80 (dd, 1H J=1.8 Hz and 10.2 Hz), 6.26-6.31 (dd, 1H J=1.8, 17 Hz), 6.44-6.51 (dd, 1H J=10.2, 17 Hz), 7.09-7.17 (m, 2H), 7.32-7.35 (dd, 1H J=1.7, 7.5 Hz), 7.48 (d, 1H J=7.1 Hz), 7.55 (s, 1H), 7.63 (d, 1H J=8.2 Hz), 7.72 (d, 1H J=8.2 Hz), 8.08 (s, 1H), 8.49 (s, 1H), 10.12 (s, 1H). MS m/z: 519.5 (ES+, M+H).

Aufarbeitung

  1. customdegassed for 10 min
  2. customagain degassed for another 5 min
  3. customThe mixture was irradiated by microwave at 80° C. for 20 min
  4. customThe reaction was quenched with water (15 mL)
  5. extractionextracted with ethyl acetate (3×10 mL)
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe crude compound was purified by prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-bb3a3ae8bd1d44fba017e9651192124f
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09145387B2

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