Sodium Carbonate → HCID 57906537, Verbindung

HRID 420496Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 420496
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[C:14](Br)=[CH:13][N:12]=[C:11]([NH2:16])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[C:14]([C:22]2[CH:21]=[CH:20][C:19]([Cl:18])=[CH:24][C:23]=2[Cl:25])=[CH:13][N:12]=[C:11]([NH2:16])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 57906440HCID 57906440, Verbindung

Produkt 1

HCID 57906537HCID 57906537, VerbindungAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

In a sealed tube, a mixture of (2-amino-5-bromo-pyridin-4-ylmethyl)-carbamic acid tert-butyl ester (4.48 g, 14.8 mmol, prepared according to Example 1, Step 1.3), 2,4-dichloro-benzeneboronic acid (4.24 g, 22.2 mmol), Pd(PPh3)4 (855 mg, 0.74 mmol) and Na2CO3 (2.0 M solution in water, 26 mL, 52.0 mmol) in DME (50 mL) was heated at 150° C. for 17 min in a microwave oven. The reaction mixture was cooled to RT, diluted in AcOEt and washed with water. The organic layer was dried over Na2SO4, filtered and evaporated. The residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→100% TBME) to yield the title compound (3.2 g, 8.7 mmol, 59%) as a white solid. MS: 368 [M−1]+; HPLC: AtRet=1.69.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to RT
  2. washwashed with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→100% TBME)

Quellen und Nachweise

ORD-Eintrag
ord-5e651189c8714aec8c4b22f9b298cc88
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097617B2

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