Diisopropylethylamine → N-(5-((2-Chlorobenzyl)thio)-4-(trifluoromethyl)thiazol-2-yl)picolinamide

HRID 716622Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 716622
Br[C:2]1[S:6][C:5]([NH:7][C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[N:4][C:3]=1[C:16]([F:19])([F:18])[F:17].C(N(C(C)C)CC)(C)C.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[Cl:71][C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][C:73]=1[CH2:78][SH:79]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Cl:71][C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][C:73]=1[CH2:78][S:79][C:2]1[S:6][C:5]([NH:7][C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[N:4][C:3]=1[C:16]([F:19])([F:18])[F:17]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 5807592-Chlorobenzyl mercaptanHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86688229N-(5-Bromo-4-(trifluoromethyl)thiazol-2-yl)picolinamide

Produkt 1

HCID 86688230N-(5-((2-Chlorobenzyl)thio)-4-(trifluoromethyl)thiazol-2-yl)picolinamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a 5 mL microwave vial was charged with N-(5-bromo-4-(trifluoromethyl)thiazol-2-yl)picolinamide (0.06 g, 0.2 mmol), diisopropylethylamine (59 μL, 0.34 mmol), Pd2(dba)3 (0.0048 g, 0.0085 mmol), Xantphos (0.0099 g, 0.017 mmol), 1,4-dioxane (0.6 mL) and 2-chlorophenylmethanethiol (22 μL, 0.17 mmol). The reaction mixture was purged with argon for 5 min; the vial was capped and heated at 100° C. for 15 h. the reaction mixture was cooled to room temperature, diluted with ethyl acetate (5 mL), filtered, washing with ethyl acetate (10 mL) and the filtrate was concentrated under vacuum. The residue was purified by column chromatography eluting with ethyl acetate/hexanes 0 to 30% to give the product.

Aufarbeitung

  1. customThe reaction mixture was purged with argon for 5 min
  2. customthe vial was capped
  3. temperaturewas cooled to room temperature
  4. additiondiluted with ethyl acetate (5 mL)
  5. filtrationfiltered
  6. washwashing with ethyl acetate (10 mL)
  7. concentrationthe filtrate was concentrated under vacuum
  8. customThe residue was purified by column chromatography
  9. washeluting with ethyl acetate/hexanes 0 to 30%
  10. customto give the product

Quellen und Nachweise

ORD-Eintrag
ord-295d2d36d9954102b79748799afa703b
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09192603B2

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