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Triethylamine → (R)-6,6-difluoro-5-[2-fluoro-5-(2-methyl-thiazol-4-ylethynyl)-phenyl]-5,7,7-trimethyl-[1,4]oxazepan-3-one

HRID 331152
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 331152
[F:1][C:2]1([F:21])[C:8]([CH3:10])([CH3:9])[O:7][CH2:6][C:5](=[O:11])[NH:4][C@@:3]1([C:13]1[CH:18]=[C:17](I)[CH:16]=[CH:15][C:14]=1[F:20])[CH3:12].[CH3:22][C:23]1[S:24][CH:25]=[C:26]([C:28]#[C:29][Si](C)(C)C)[N:27]=1.C(N(CC)CC)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)C=O>[F:1][C:2]1([F:21])[C:8]([CH3:10])([CH3:9])[O:7][CH2:6][C:5](=[O:11])[NH:4][C@@:3]1([C:13]1[CH:18]=[C:17]([C:29]#[C:28][C:26]2[N:27]=[C:23]([CH3:22])[S:24][CH:25]=2)[CH:16]=[CH:15][C:14]=1[F:20])[CH3:12]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 3

HCID 8471TriethylamineHCID 109214422-Methyl-4-(2-(trimethylsilyl)ethynyl)-1,3-thiazoleHCID 68380642(R)-6,6-difluoro-5-(2-fluoro-5-iodo-phenyl)-5,7,7-trimethyl-[1,4]oxazepan-3-one

Produkt 1

HCID 68379907(R)-6,6-difluoro-5-[2-fluoro-5-(2-methyl-thiazol-4-ylethynyl)-phenyl]-5,7,7-trimethyl-[1,4]oxazepan-3-oneAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 11776
Triphenylphosphine
Katalysator
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator
HCID 67553Tetrabutylammonium IodideKatalysator
HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysator
HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A dried pressure tube was charged with (R)-6,6-difluoro-5-(2-fluoro-5-iodo-phenyl)-5,7,7-trimethyl-[1,4]oxazepan-3-one (intermediate B6″.1) (203 mg, 491 μmol), 2-methyl-4-((trimethylsilyl)ethynyl)thiazole (115 mg, 590 μmol), and N,N-dimethylformamide (3 ml) flushed with nitrogen (solution 1). Another dried pressure tube was flushed with argon, thereafter, successively N,N-dimethylformamide (3 ml), bis(triphenylphosphine) palladium(II)chloride (24.6 mg, 34.4 μmol), triphenylphoshine (5.2 mg, 19.7 μmol), copper(I)iodide (1.9 mg, 9.8 μmol), triethylamine (249 mg, 2.46 mmol), and tetrabutylammoniumiodide (185 mg, 491 μmol) were added. The mixture was heated to 40° C., and solution 1 was added dropwise. The temperature was raised to 60° C. and stirring was continued for 16 hours. For the workup, the reaction mixture was evaporated at reduced pressure and the residue directly purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 50:50 as the eluent. The (R)-6,6-difluoro-5-[2-fluoro-5-(2-methyl-thiazol-4-ylethynyl)-phenyl]-5,7,7-trimethyl-[1,4]oxazepan-3-one (182 mg, 91% yield) was obtained as a white foam. MS (ISP): m/z=409.3 [M+H]+.

Aufarbeitung

  1. customflushed with nitrogen (solution 1)
  2. customAnother dried pressure tube was flushed with argon
  3. temperatureThe temperature was raised to 60° C.
  4. customFor the workup, the reaction mixture was evaporated at reduced pressure
  5. customthe residue directly purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 50:50 as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-8e817188ba6840c3b1abcf874949eb57
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08877744B2

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