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Sodium Carbonate → 6-(4-Carboxyphenyl)-8-(4-benzo[c]furazanyl)-1,7-naphthyridine

HRID 369038
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 369038
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:17](=[C:18](Br)[N:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)=[CH:6][CH:5]=1)([OH:3])=[O:2].[N:21]1[O:22][N:23]=[C:24]2[C:29](B(O)O)=[CH:28][CH:27]=[CH:26][C:25]=12.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:17](=[C:18]([C:29]4[C:24]5[C:25](=[N:21][O:22][N:23]=5)[CH:26]=[CH:27][CH:28]=4)[N:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)=[CH:6][CH:5]=1)([OH:3])=[O:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 80271Tri-o-tolylphosphineHCID 21186805B-2,1,3-Benzoxadiazol-4-ylboronic acidHCID 232846464-(8-Bromo-1,7-naphthyridin-6-yl)benzoic acid

Produkt 1

HCID 232846386-(4-Carboxyphenyl)-8-(4-benzo[c]furazanyl)-1,7-naphthyridineAusbeute 60,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 6-(4-carboxyphenyl)-8-bromo-1,7-naphthyridine (100 mg, 0.304 mmol) in DMF (2.5 ml) is added 4-benzo[c]furazanyl boronic acid (60 mg, 0.36 mmol), bis(dibenzylidenacetone) palladium (7 mg, 0.0122 mmol), tri-o-tolylphosphine (7.4 mg, 0.024 mmol) and aqueous Na2CO3 (0.9 ml, 2N). The reaction mixture is stirred at 80° for 2 h. The hot solution is filtred through cellit and the solution evaporated to dryness. The residue is stirred in ethyl acetate (20 ml), the suspension is filtered and the organic solvent is removed. The residue is dissolved in hot DMF (7 ml) and the crude product is precipitated by carefully adding aqueous HCl (2N, 1 ml). The crude product in recrystallized from hot DMF to yield the title compound (68 mg). MH+369; Melting point >300° C. M+H=369. Retention time HPLC=10.40 min (column: LiChroCart 125-4, Supersphere 60 RP-select B, 40°; eluent: acetonitril-water (0.1% TFA)=45:55; 1 ml/min; detection at 254 nm).

Aufarbeitung

  1. customthe solution evaporated to dryness
  2. stirringThe residue is stirred in ethyl acetate (20 ml)
  3. filtrationthe suspension is filtered
  4. customthe organic solvent is removed
  5. dissolutionThe residue is dissolved in hot DMF (7 ml)
  6. customthe crude product is precipitated by carefully adding aqueous HCl (2N, 1 ml)
  7. customThe crude product in recrystallized from hot DMF

Quellen und Nachweise

ORD-Eintrag
ord-3e909dee7bf24e4f821be6c1c311f31c
Quelldatensatz
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06136821

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