Nitrogen → N-{[2-(cyclopropylethynyl)-1,3-thiazol-4-yl]methoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

HRID 1258559

Reaktionsgleichung

Reaktionsgleichung von HRID 1258559
Br[C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8][N:9]=[C:10]([C:17]2[N:21]([CH3:22])[N:20]=[N:19][N:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1.N#N.[CH:25]1([C:28]#[CH:29])[CH2:27][CH2:26]1.C(N(C(C)C)C(C)C)C>C1COCC1.CCOC(C)=O.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:25]1([C:28]#[C:29][C:2]2[S:3][CH:4]=[C:5]([CH2:7][O:8][N:9]=[C:10]([C:17]3[N:21]([CH3:22])[N:20]=[N:19][N:18]=3)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:6]=2)[CH2:27][CH2:26]1

Komponenten

9

Edukt 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 138823CyclopropylacetyleneHCID 86649974N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

Produkt 1

HCID 86653115N-{[2-(cyclopropylethynyl)-1,3-thiazol-4-yl]methoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimineAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (1 g, 2.63 mmol, 1 eq.) in 20 ml dry THF “degassed” with N2, was added cyclopropylacetylene (70%, 0.996 g, 10.54 mmol, 4 eq.) followed by N-ethyldiisopropylamine (1.36 g, 10.54 mmol, 4 eq.), Copper(I) Iodide (0.025 g, 0.132 mmol, 0.05 eq.) and Tetrakis(triphenylphosphine)palladium (0.152 g, 0.132 mmol, 0.05 eq.). The reaction was stirred for 20 hrs at room temperature for complete conversion. The reaction mixture was diluted with EtOAc (50 ml), filtered through “Chem Elut” cartridge, washed with fresh EtOAc (2×20 ml) and the filtrate was evaporated. The residue was purified by chromatography on silica gel to give N-{[2-(cyclopropylethynyl)-1,3-thiazol-4-yl]methoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.57 g, 60% yield, single stereoisomer) as a brown gum.

Aufarbeitung

  1. filtrationfiltered through “Chem Elut” cartridge
  2. washwashed with fresh EtOAc (2×20 ml)
  3. customthe filtrate was evaporated
  4. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-81021db69605417684d16fe436fa6423
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466176B2

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