Dimethylformamide → 5-Cyclopentenyl-6-(cyclopropylmethoxy)-pyridine-2-carboxylic acid

HRID 632031Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 632031
Br[C:2]1[CH:3]=[CH:4][C:5]([C:13]([OH:15])=[O:14])=[N:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][CH2:11]1.[C:16]1(B2OC(C)(C)C(C)(C)O2)[CH2:20][CH2:19][CH2:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].CN(C=O)C>O.C(Cl)Cl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:16]1([C:2]2[CH:3]=[CH:4][C:5]([C:13]([OH:15])=[O:14])=[N:6][C:7]=2[O:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)[CH2:20][CH2:19][CH2:18][CH:17]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 154866112-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 710875435-Bromo-6-cyclopropylmethoxy-pyridine-2-carboxylic acid

Produkt 1

HCID 710874455-Cyclopentenyl-6-(cyclopropylmethoxy)-pyridine-2-carboxylic acidAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

The mixture of 5-bromo-6-(cyclopropylmethoxy)-pyridine-2-carboxylic acid (Example 9 d, 1.0 g, 4 mmol), 2-cyclopentenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAN 287944-10-9, 0.86 g, 4 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride methylene chloride complex (CAN 95464-05-4, 150 mg 0.18 mmol) and aqueous sodium carbonate solution (2N, 16 mL) was added to DMF (10 ml). The mixture was heated to 100° C. overnight; then the solution was diluted with water (15 mL), extracted with ethyl acetate (30 mL), the water layer was adjusted to pH=3.0 by hydrochloric acid (3N) and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with water (2×100 mL) and brine (80 mL) and evaporated to dryness. The residue was purified by column chromatography (silica gel, 8 g, eluting with 15% ethyl acetate in petroleum ether) to obtain the product (0.85 g, 89%) as a white solid; MS (LC/MS): 260.1 [M+H]+.

Aufarbeitung

  1. extractionextracted with ethyl acetate (30 mL)
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washThe combined organic layers were washed with water (2×100 mL) and brine (80 mL)
  4. customevaporated to dryness
  5. customThe residue was purified by column chromatography (silica gel, 8 g, eluting with 15% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-b4735cc8f09a4ad2aed1e92c649da207
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321727B2

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