Triethylamine → 8-Fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-9-vinyl-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene

HRID 1530728Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1530728
Br[C:2]1[C:3]([F:25])=[CH:4][C:5]2[O:14][CH2:13][CH2:12][N:11]3[C:7](=[N:8][C:9]([C:15]4[N:16]([CH:21]([CH3:23])[CH3:22])[N:17]=[C:18]([CH3:20])[N:19]=4)=[CH:10]3)[C:6]=2[CH:24]=1.[CH:26]([B-](F)(F)F)=[CH2:27].[K+].C(N(CC)CC)C>C(O)CC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:25][C:3]1[C:2]([CH:26]=[CH2:27])=[CH:24][C:6]2[C:7]3[N:11]([CH2:12][CH2:13][O:14][C:5]=2[CH:4]=1)[CH:10]=[C:9]([C:15]1[N:16]([CH:21]([CH3:23])[CH3:22])[N:17]=[C:18]([CH3:20])[N:19]=1)[N:8]=3

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 6831287410-Bromo-9-fluoro-2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

Produkt 1

HCID 683126378-Fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-9-vinyl-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azuleneAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 10311-PropanolLösungsmittel

Versuchsvorschrift

A degassed solution of 9-bromo-8-fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene from Example 8 (5.0 g, 12.31 mmol), potassium vinyltrifluoroborate (2.47 g, 18.46 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (1.01 g, 1.23 mmol) and triethylamine (8.58 mL, 61.55 mmol) in nPrOH (50 mL) was heated to 100° C. for 2 h. The reaction mixture was concentrated in vacuo; the residue was taken up in EtOAc and filtered through celite. Organics were washed with water and brine, dried (Na2SO4) and concentrated in vacuo to give the title compound (3.82 g, 10.81 mmol, 88%) as a peach solid. The product was taken on without further purification. LCMS (Method J): RT=3.35 min, [M+H]+ =354.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. filtrationfiltered through celite
  3. washOrganics were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-66014584fb64468b9508bf2a14bafc0d
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090628B2

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