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Boron tribromide → 7-(2-Hydroxyethoxy)-4-(2-methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-9H-pyrido[3,4-b]indole-1-carboxamide

HRID 2361280
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Reaktionsgleichung von HRID 2361280
C[O:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]3[C:18]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([N:25]5[C:34](=[O:35])[C:33]6[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=6)[N:27]=[CH:26]5)[C:20]=4[CH3:36])=[CH:17][N:16]=[C:15]([C:37]([NH2:39])=[O:38])[C:11]=3[NH:12]2)=[CH:8][CH:7]=1.BrB(Br)Br>ClCCl>[OH:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]3[C:18]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([N:25]5[C:34](=[O:35])[C:33]6[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=6)[N:27]=[CH:26]5)[C:20]=4[CH3:36])=[CH:17][N:16]=[C:15]([C:37]([NH2:39])=[O:38])[C:11]=3[NH:12]2)=[CH:8][CH:7]=1
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Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 706516047-(2-Methoxyethoxy)-4-(2-methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-9H-pyrido[3,4-b]indole-1-carboxamide

Produkt 1

HCID 866815177-(2-Hydroxyethoxy)-4-(2-methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-9H-pyrido[3,4-b]indole-1-carboxamideAusbeute 43,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 7-(2-methoxyethoxy)-4-(2-methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-9H-pyrido[3,4-b]indole-1-carboxamide (101 mg, 0.194 mmol) in dichloromethane (5 mL) at 0° C. was added tribromoborane in dichloromethane (0.622 mL, 0.622 mmol) over 5 min. The resulting heterogeneous mixture was stirred at room temperature for 1.5 hr. The reaction was quenched with ice water (15 mL). The mixture was basified with 1 N NaOH solution to pH 10 and extracted with ethyl acetate (3×40 mL). The combined extract was washed with brine (30 mL) and dried over anhydrous MgSO4. After the solvent was removed under vacuum, the residue was purified by reverse phase HPLC. The correct fraction was concentrated under vacuum, basified with saturated NaHCO3 solution, and extracted with ethyl acetate (3×30 mL). The combined extract was washed with brine (30 mL) and dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (44.0 mg, 0.084 mmol, 43.3% yield) as a yellow solid. The product is mixture of two atropisomers at rt. LCMS (M+H)+=506.23. 1H NMR (500 MHz, DMSO-d6) (recognizable peaks for the major atropisomer) δ: 11.67 (s, 1H), 8.44 (s, 1H), 8.21 (s, 1H), 7.37 (s, 1H), 4.07 (m, 2H), 3.78 (m, 2H), 1.81 (s, 3H).

Aufarbeitung

  1. customThe reaction was quenched with ice water (15 mL)
  2. extractionextracted with ethyl acetate (3×40 mL)
  3. extractionThe combined extract
  4. washwas washed with brine (30 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. customAfter the solvent was removed under vacuum
  7. customthe residue was purified by reverse phase HPLC
  8. concentrationThe correct fraction was concentrated under vacuum
  9. extractionextracted with ethyl acetate (3×30 mL)
  10. extractionThe combined extract
  11. washwas washed with brine (30 mL)
  12. dry with materialdried over anhydrous MgSO4
  13. customRemoval of solvent under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a6f3b1b53bea446d89b850422b5722fa
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08685969B2

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