Propargyl alcohol → HCID 178432388, Verbindung

HRID 2120768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2120768
Br[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][C:11]=1[CH3:12])[N:8]=[CH:7][C:6]([C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)=[O:14])=[C:5]2[OH:24].[CH2:25]([OH:28])[C:26]#[CH:27].C(N(CC)CC)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][NH:15][C:13]([C:6]2[CH:7]=[N:8][C:9]3[C:4]([C:5]=2[OH:24])=[CH:3][C:2]([C:27]#[C:26][CH2:25][OH:28])=[C:11]([CH3:12])[N:10]=3)=[O:14])=[CH:18][CH:19]=1

Komponenten

6

Edukt 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 178432387HCID 178432387, Verbindung

Produkt 1

HCID 178432388HCID 178432388, VerbindungAusbeute 35,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 6-bromo-N-(4-chlorobenzyl)-4-hydroxy-7-methyl[1,8]naphthyridine-3-carboxamide (0.244 g, 0.60 mmol), propargyl alcohol (0.047 g, 0.84 mmol), triethylamine (0.38 mL) and PdCl2(PPh3)2 (0.023 g, 0.03 mmol) in 3 mL DMF is heated to 90° C. for 2.5 h. The resulting solution is cooled and partitioned between EtOAc and water. The solid which formed is filtered and discarded. The aqueous layer is extracted with EtOAc (3×). The combined organic layers are washed with brine, dried and condensed. The crude product is chromatographed on silica (Biotage flash 40S, eluent 2% MeOH/CH2Cl2 then 3% MeOH/CH2Cl2. Fractions homogeneous by TLC are combined and condensed to yield 0.081 g (35%) of the desired product as a yellow solid. Physical characteristics are as follows: m.p. 279-281° C. (dec.); 1H NMR (DMSO-d6) δ13.19, 10.12, 8.64, 8.43, 7.38, 5.46, 4.54, 4.40, 2.71; IR (drift) 3194, 3065, 2944, 1645, 1597, 1566, 1522, 1488, 1418, 1357, 1257, 1208, 1015, 851, 809 cm−1; OAMS supporting ions at: ESI+ 381.9 ESI− 379.9; HRMS (FAB) calcd for C20H16CIN3O3 +H1 382.0958, found 382.0960.

Aufarbeitung

  1. temperatureThe resulting solution is cooled
  2. custompartitioned between EtOAc and water
  3. customThe solid which formed
  4. filtrationis filtered
  5. extractionThe aqueous layer is extracted with EtOAc (3×)
  6. washThe combined organic layers are washed with brine
  7. customdried
  8. customcondensed
  9. customThe crude product is chromatographed on silica (Biotage flash 40S, eluent 2% MeOH/CH2Cl2
  10. customcondensed

Quellen und Nachweise

ORD-Eintrag
ord-9528541ec700436eaa8dd1855d4889d3
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06693114B2

Notizen zur Reaktion

Wird geladen…