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tert-Butyl 2-(9-iodo-7-(4-Isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate → tert-Butyl 2-(7-(4-Isopropoxy-3-(trifluoromethyl)benzyloxy)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

HRID 515707
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 515707
I[C:2]1[C:10]2[CH:9]=[C:8]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:14]=3)[CH:7]=[CH:6][C:5]=2[N:4]2[CH2:27][CH2:28][CH:29]([CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:3]=12.[CH3:38][Zn]C>C1COCC1>[CH:20]([O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][O:11][C:8]2[CH:7]=[CH:6][C:5]3[N:4]4[CH2:27][CH2:28][CH:29]([CH2:30][C:31]([O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:32])[C:3]4=[C:2]([CH3:38])[C:10]=3[CH:9]=2)=[CH:14][C:15]=1[C:23]([F:26])([F:24])[F:25])([CH3:21])[CH3:22]
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Komponenten

4

Edukt 2

HCID 67251011tert-Butyl 2-(9-iodo-7-(4-Isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetateHCID 178477796HCID 178477796, Verbindung

Produkt 1

HCID 67249074tert-Butyl 2-(7-(4-Isopropoxy-3-(trifluoromethyl)benzyloxy)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetateAusbeute 57,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 2-(9-iodo-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (0.778 g, 1.236 mmol) in THF (12.3 mL) under nitrogen was added 2 M solution of dimethylzinc (1.854 mL, 3.71 mmol), followed by bis(tri-t-butylphosphine)Pd(0) (0.057 g, 0.111 mmol). The reaction was stirred overnight, slowly quenched with saturated NaHCO3, diluted with EtOAc, and filtered through Celite®. The organics were washed with water (twice), brine, dried over MgSO4, and filtered. The solvent was removed under vacuum. The residue was purified by silica gel column chromatography to give the title compound as a solid (0.366 g). LCMS m/z=518.6 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.28 (d, J=5.94 Hz, 6H), 1.38 (s, 9H), 2.15 (s, 3H), 2.19-2.30 (m, 1H), 2.43-2.48 (m, 1H), 2.69-2.81 (m, 2H), 3.54-3.64 (m, 1H), 3.86-3.96 (m, 1H), 3.98-4.07 (m, 1H), 4.73-4.84 (m, 1H), 5.07 (s, 2H), 6.74 (dd, J=8.65, 2.34 Hz, 1H), 7.00 (d, J=2.27 Hz, 1H), 7.13 (d, J=8.72 Hz, 1H), 7.29 (d, J=9.35 Hz, 1H), 7.64-7.71 (m, 2H).

Aufarbeitung

  1. customslowly quenched with saturated NaHCO3
  2. additiondiluted with EtOAc
  3. filtrationfiltered through Celite®
  4. washThe organics were washed with water (twice), brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed under vacuum
  8. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e8b18e673791439689fc03dfdb66fa79
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09108969B2

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