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Sodium Bicarbonate → t-Butyl 4-{4-[({2-[(t-butoxycarbonyl)amino]phenyl}amino)carbonyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate

HRID 888045
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 888045
C(=O)([O-])O.[Na+].FC(F)(F)S(O[C:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH:17]=1)(=O)=O.[C:27]([O:31][C:32]([NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[NH:41][C:42](=[O:58])[C:43]1[CH:48]=[CH:47][C:46](B2OC(C)(C)C(C)(C)O2)=[CH:45][CH:44]=1)=[O:33])([CH3:30])([CH3:29])[CH3:28]>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:27]([O:31][C:32]([NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[NH:41][C:42]([C:43]1[CH:48]=[CH:47][C:46]([C:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH:17]=2)=[CH:45][CH:44]=1)=[O:58])=[O:33])([CH3:30])([CH3:28])[CH3:29]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 59830883N-(2-t-Butoxycarbonylaminophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Produkt 1

HCID 68407877t-Butyl 4-{4-[({2-[(t-butoxycarbonyl)amino]phenyl}amino)carbonyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylateAusbeute 74,3 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A saturated solution of sodium hydrogen carbonate (3 ml) was added to a stirred solution of t-butyl 4-{[(trifluoromethyl)sulfonyl]oxy}-3,6-dihydropyridine-1(2H)-carboxylate (Method 72, 200 mg, 0.60 mmol) in 1,2-dimethoxyethane (3 ml). N-(2-t-butoxycarbonylaminophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Method 13) (318 mg, 0.72 mmol) was added followed by tetrakis(triphenylphosphine) palladium (100 mg, 0.09 mmol) and the mixture stirred at 80° C. for 18 hours. The cooled mixture was partitioned between ethyl acetate and water. The organic phase was separated, then washed with water and dried over magnesium sulfate, filtered and evaporated. The resultant residue was purified by flash column chromatography (eluting with 0-15% methanol in dichloromethane) to give the title compound (220 mg, 74%); NMR Spectrum: (DMSO-d6) 1.42 (s, 9H), 1.43 (s, 9H), 2.48 (m, 2H), 3.55 (m, 2H), 4.02 (m, 2H), 6.31 (s, 1H), 7.17 (m, 2H), 7.52 (m, 2H), 7.58 (d, 2H), 7.92 (d, 2H), 8.62 (s, 1H), 9.79 (s, 1H); Mass Spectrum: M+H+ 494.

Aufarbeitung

  1. customThe cooled mixture was partitioned between ethyl acetate and water
  2. customThe organic phase was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe resultant residue was purified by flash column chromatography (eluting with 0-15% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-9e249831663449c38213aca4e73a6e1d
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08247562B2

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