Ammonium Chloride → trans-N-(7-Chloro-2,3,4,14b-tetrahydro12-methyl-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide

HRID 16181

Reaktionsgleichung

Reaktionsgleichung von HRID 16181
Br[C:2]1[CH:28]=[CH:27][C:5]2[C@@H:6]3[C@H:19]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH2:18][CH2:17][CH2:16][N:7]3[C:8]3[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:9]=3[O:10][C:4]=2[CH:3]=1.[Cl-].[CH3:30][Zn+].[NH4+].[Cl-]>C1COCC1.[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].Cl[Pd]Cl>[Cl:15][C:13]1[CH:12]=[CH:11][C:9]2[O:10][C:4]3[CH:3]=[C:2]([CH3:30])[CH:28]=[CH:27][C:5]=3[C@@H:6]3[C@H:19]([NH:20][C:21](=[O:26])[C:22]([F:23])([F:25])[F:24])[CH2:18][CH2:17][CH2:16][N:7]3[C:8]=2[CH:14]=1

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 86599893HCID 86599893, VerbindungHCID 178477797HCID 178477797, Verbindung

Produkt 1

HCID 86599892trans-N-(7-Chloro-2,3,4,14b-tetrahydro12-methyl-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 131728027Ferrocene palladium dichlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of trans-N-(12-bromo-7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido-[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide (80 mg, 0.17 mmol) in THF (2 mL) was added ferrocene PdCl2 (5 mg, 7 μmol), and the reaction mixture was stirred for 5 min. Methylzinc chloride was added dropwise whereafter the reaction mixture was heated to 60° C. and stirred overnight at 60° C. The mixture was poured into sat (aq) NH4Cl and extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried (Na2SO4) and evaporated. After purification on silica and with HPLC the title compound was obtained (13.2 mg, 19%). Data: 1H-NMR (400 MHz, DMSO) 1.60-1.85 (m, 3H), 2.0 (m, 1H), 2.23 (s, 3H), 3.11 (td, J=2.8, 13.2, 1H), 3.85 (d, J=14, 1H), 4.10 (d, J=10, 1H), 4.40 (m, 1H), 6.69-7.10 (6 ArH), 9.16 (d, J=10, 1H).

Aufarbeitung

  1. stirringstirred overnight at 60° C
  2. additionThe mixture was poured
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customAfter purification on silica

Quellen und Nachweise

ORD-Eintrag
ord-74de55984cef41bc8c4b69e2239e6d49
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737136B2

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