Silane, (ethenyloxy)trimethyl- → 2-(4-(7-Chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4'-piperidine]-1'-ylcarbon-yl)-2-methoxyphenyl)acetaldehyde

HRID 2204278

Reaktionsgleichung

Reaktionsgleichung von HRID 2204278
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:28][CH2:27][C:13]3([C:18]4=[CH:19][CH:20]=[CH:21][N:17]4[C:16]4[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:15]=4[O:14]3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[O:29][CH3:30].C[Si](C)(C)[O:33][CH:34]=[CH2:35]>CN(C=O)C.F[Zn]F>[Cl:26][C:24]1[CH:23]=[CH:22][C:16]2[N:17]3[CH:21]=[CH:20][CH:19]=[C:18]3[C:13]3([CH2:27][CH2:28][N:10]([C:8]([C:5]4[CH:6]=[CH:7][C:2]([CH2:35][CH:34]=[O:33])=[C:3]([O:29][CH3:30])[CH:4]=4)=[O:9])[CH2:11][CH2:12]3)[O:14][C:15]=2[CH:25]=1

Komponenten

5

Edukt 2

HCID 80344Silane, (ethenyloxy)trimethyl-HCID 58551353(4-Bromo-3-methoxy-phenyl)-(7'-chlorospiro[piperidine-4,4'-pyrrolo[2,1-c][1,4]benzoxazine]-1-yl)methanone

Produkt 1

HCID 585508322-(4-(7-Chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4'-piperidine]-1'-ylcarbon-yl)-2-methoxyphenyl)acetaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24551Zinc fluorideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a microwave vial was added Pd(tBu3P)2 (128 mg, 0.250 mmol) and difluorozinc (259 mg, 2.50 mmol). The vial was capped and purged with nitrogen for 10 minutes. DMF (1 mL) was added and the mixture was stirred for 10 minutes. A solution of (4-bromo-3-methoxy-phenyl)-(7′-chlorospiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1-yl)methanone (244 mg, 0.500 mmol) in DMF (1.5 mL) was added followed by trimethyl(vinyloxy)silane (581 mg, 5.00 mmol). The reaction mixture was heated at 80° C. for 1 h before it was quenched with brine and extracted with EtOAc (3×). The combined organic layers were dried over sodium sulfate and the solvent was removed. The crude reaction was purified by silica gel chromatography (5%-80% ethyl acetate/hexanes) to give 2-(4-(7-chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-ylcarbon-yl)-2-methoxyphenyl)acetaldehyde.

Aufarbeitung

  1. customThe vial was capped
  2. custompurged with nitrogen for 10 minutes
  3. additionDMF (1 mL) was added
  4. customwas quenched with brine
  5. extractionextracted with EtOAc (3×)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. customthe solvent was removed
  8. customThe crude reaction
  9. customwas purified by silica gel chromatography (5%-80% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-4724fffb38d744c698369222badefdf1
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365588B2

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