Sodium Carbonate Monohydrate → N-(7-(3-Fluoro-4-methoxyphenyl)benzo[d]thiazol-2-yl)acetamide

HRID 2077516

Reaktionsgleichung

Reaktionsgleichung von HRID 2077516
Br[C:2]1[C:10]2[S:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.Br[C:16]1[CH:28]=[CH:27][C:19]2[N:20]=[C:21]([NH:23][C:24](=[O:26])[CH3:25])[S:22][C:18]=2[CH:17]=1.[F:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][C:35]=1[O:36][CH3:37].O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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.CCO.O>[F:29][C:30]1[CH:31]=[C:32]([C:2]2[C:10]3[S:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[N:7][C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH:33]=[CH:34][C:35]=1[O:36][CH3:37].[F:29][C:30]1[CH:31]=[C:32]([C:16]2[CH:28]=[CH:27][C:19]3[N:20]=[C:21]([NH:23][C:24](=[O:26])[CH3:25])[S:22][C:18]=3[CH:17]=2)[CH:33]=[CH:34][C:35]=1[O:36][CH3:37]

Komponenten

10

Edukt 4

HCID 2735133Sodium Carbonate MonohydrateHCID 27821943-Fluoro-4-methoxyphenylboronic acidHCID 3240669N-(6-bromo-1,3-benzothiazol-2-yl)acetamideHCID 57584914N-(7-bromobenzo[d]thiazol-2-yl)acetamide

Produkt 2

HCID 57584946N-(7-(3-Fluoro-4-methoxyphenyl)benzo[d]thiazol-2-yl)acetamideHCID 86627994N-(6-(3-Fluoro-4-methoxyphenyl)benzo[d]thiazol-2-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

The mixture (302.6 mg, 1.116 mmol) of N-(7-bromobenzo[d]thiazol-2-yl)acetamide and N-(6-bromobenzo[d]thiazol-2-yl)acetamide, 3-fluoro-4-methoxyphenylboronic acid (298 mg, 1.75 mmol), sodium carbonate monohydrate (0.247 mL, 4.48 mmol), and dichlorobis(triphenylphosphine)palladium (II) (168 mg, 0.239 mmol) were suspended in 1,2-dimethoxyethane (3.5 mL), water (1.5 mL) and EtOH (1.0 mL). The reaction flask was fit with a reflux condensor and placed in a preheated oil bath (85° C.) and stirred under argon for 1 hour. The reaction was cooled to room temperature and allowed to stand overnight. It was then filtered through a Celite® (diatomaceous earth) pad, and the solid was washed with MeOH, DCM, and DME. The filtrate was concentrated and treated with DCM. The resulting precipitate was collected by filtration and the crude was further purified by HPLC to provide N-(7-(3-Fluoro-4-methoxyphenyl)benzo[d]thiazol-2-yl)acetamide and N-(6-(3-Fluoro-4-methoxyphenyl)benzo[d]thiazol-2-yl)acetamide.

Aufarbeitung

  1. customplaced in a preheated oil bath
  2. temperatureThe reaction was cooled to room temperature
  3. waitto stand overnight
  4. filtrationIt was then filtered through a Celite® (diatomaceous earth) pad
  5. washthe solid was washed with MeOH, DCM, and DME
  6. concentrationThe filtrate was concentrated
  7. additiontreated with DCM
  8. filtrationThe resulting precipitate was collected by filtration
  9. customthe crude was further purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-79222293d2ca422582a2e4ede6183025
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928140B2

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