Potassium Phosphate, Tribasic → 2-(8-tert-Butyl-5-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-6-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-benzaldehyde

HRID 1879674Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1879674
Br[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[C:16](=[O:17])[C:15]3[CH:18]=[CH:19][C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:21][C:14]=3[NH:13][CH2:12][CH2:11]2)[C:3]=1[CH:4]=[O:5].[CH3:26][N:27]1[CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:30]=[C:29]([NH:42][C:43]2[CH:48]=[CH:47][C:46]([C:49]([N:51]3[CH2:56][CH2:55][O:54][CH2:53][CH2:52]3)=[O:50])=[CH:45][N:44]=2)[C:28]1=[O:57].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.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(O)CCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[C:22]([C:20]1[CH:19]=[CH:18][C:15]2[C:16](=[O:17])[N:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:2]([C:31]4[CH:30]=[C:29]([NH:42][C:43]5[CH:48]=[CH:47][C:46]([C:49]([N:51]6[CH2:56][CH2:55][O:54][CH2:53][CH2:52]6)=[O:50])=[CH:45][N:44]=5)[C:28](=[O:57])[N:27]([CH3:26])[CH:32]=4)[C:3]=3[CH:4]=[O:5])[CH2:11][CH2:12][NH:13][C:14]=2[CH:21]=1)([CH3:24])([CH3:23])[CH3:25]

Komponenten

7

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 592164661-Methyl-3-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyridin-2-oneHCID 595485362-Bromo-6-(8-tert-butyl-5-oxo-1,2,3,5-tetrahydrobenzo[e][1,4]diazepin-4-yl)-benzaldehyde

Produkt 1

HCID 595485292-(8-tert-Butyl-5-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-6-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysatorHCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2-Bromo-6-(8-tert-butyl-5-oxo-1,2,3,5-tetrahydrobenzo[e][1,4]diazepin-4-yl)-benzaldehyde (0.100 g, 0.23 mmol),1-Methyl-3-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyridin-2-one (0.091 g, 1.0 eq), xantphos (12 mg, 0.09 eq), and potassium phosphate (0.096 g, 2 eq) were taken up in n-butanol (3 mL) and water (0.5 mL) and a stream of argon was bubbled through the mixture for 1 minute. Pd(dba)2 (0.008 g, 0.06 eq) was added and argon was bubbled through for an additional minute. The reaction was heated under argon and stirred at 100° C. for 3 hours. The reaction was cooled, solvent was removed under vacuum, and placed directly on a silica gel column, eluted with 100% ethyl acetate, then 4% MeOH in CH2Cl2 to give the title compound as a brown solid, 76 mg as a 60:40 mixture (the title compound as the major component) with an impurity and used without further purification.

Aufarbeitung

  1. customwater (0.5 mL) and a stream of argon was bubbled through the mixture for 1 minute
  2. customargon was bubbled through for an additional minute
  3. temperatureThe reaction was heated under argon
  4. temperatureThe reaction was cooled
  5. customsolvent was removed under vacuum
  6. washeluted with 100% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-60c9bd9eaa1f465dbf24f0519fe61950
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318719B2

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