Sodium Carbonate → Methyl 6-(6-hydroxynaphthalen-2-yl)nicotinate

HRID 1771453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1771453
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7](B(O)O)[CH:6]=[CH:5]2.Br[C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:17]=1)[CH:6]=[CH:5]2

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 4349738(6-Hydroxynaphthalen-2-yl)boronic acidHCID 13349623Methyl 6-bromopyridine-3-carboxylate

Produkt 1

HCID 136331263Methyl 6-(6-hydroxynaphthalen-2-yl)nicotinate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 18180031Water 1,2-dimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 6-hydroxynaphthalen-2-ylboronic acid (250 mg, 1.33 mmol), methyl 6-bromonicotinate (260 mg, 1.21 mmol), Pd(dppf)Cl2 (90 mg, 0.12 mmol) and sodium carbonate (205 mg, 2.41 mmol) in DME/water (3 mL/1 mL) was heated to 120° C. by microwave for 1 h. Then the mixture was partitioned with water (10 mL) and EA (20 mL). The precipitate was filtered off. The organic phase was separated, washed with brine (15 mL), dried over Na2SO4 and concentrated to afford product (crude, 380 mg) as a brown oil.

Aufarbeitung

  1. customThen the mixture was partitioned with water (10 mL) and EA (20 mL)
  2. filtrationThe precipitate was filtered off
  3. customThe organic phase was separated
  4. washwashed with brine (15 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto afford product (crude, 380 mg) as a brown oil

Quellen und Nachweise

ORD-Eintrag
ord-3c534e60dcc64abb98b11ca9c1b020cb
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249132B2

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