Sodium Carbonate → tert-butyl(6bR,10aS)-5-(2,3-dichlorophenyl)-1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole carboxylate

HRID 51029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 51029
Br[C:2]1[CH:3]=[C:4]2[C:8]3=[C:9]([S:11][CH2:12][CH2:13][N:7]3[C@H:6]3[CH2:14][CH2:15][N:16](C(OC(C)(C)C)=O)[CH2:17][C@@H:5]23)[CH:10]=1.[Cl:25][C:26]1[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O.[C:36]([O-:39])([O-])=[O:37].[Na+].[Na+]>C1C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:25][C:26]1[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=1[C:2]1[CH:3]=[C:4]2[C:8]3=[C:9]([S:11][CH2:12][CH:13]([C:36]([O:39][C:4]([CH3:8])([CH3:5])[CH3:3])=[O:37])[N:7]3[C@H:6]3[CH2:14][CH2:15][N:16]=[CH:17][C@H:5]23)[CH:10]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27346612,3-Dichlorobenzeneboronic acidHCID 21302667tert-butyl(6bR,10aS)-5-bromo-1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole-8(7H)-carboxylate

Produkt 1

HCID 86759404tert-butyl(6bR,10aS)-5-(2,3-dichlorophenyl)-1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole carboxylateAusbeute 159,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of tert-butyl(6bR,10aS)-5-bromo-1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole-8(7H)-carboxylate (150 mg, 0.37 mmol) and 2,3-dichlorophenylboronic acid (143 mg, 0.75 mmol) in benzene (10 mL) and 2M Na2CO3 aqueous solution (0.74 mL, 1.48 mmol) was degassed at 20° C. Pd(PPh3)2Cl2 (7.8 mg, 0.01 mmol) was added, and the reaction mixture was degassed one more time. The reaction mixture was refluxed for 15 h then cooled to 20° C. The reaction mixture was diluted with EtOAc and washed with saturated NaHCO3 and brine. The combined organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed (silica gel; Hexane:EtOAc 3:1) to give tert-butyl(6bR,10aS)-5-(2,3-dichlorophenyl)-1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole carboxylate as a light yellow solid (140 mg, 81%).

Aufarbeitung

  1. customthe reaction mixture was degassed one more time
  2. temperatureThe reaction mixture was refluxed for 15 h
  3. additionThe reaction mixture was diluted with EtOAc
  4. washwashed with saturated NaHCO3 and brine
  5. dry with materialThe combined organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed (silica gel; Hexane:EtOAc 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-7f90b6bb0bb34dd9969f9edfddb20b5a
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713471B1

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