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

HRID 2077516

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HRID 2077516 반응식
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]

참가 물질

10

반응물 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

생성물 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

시약·촉매·용매 4

HCID 178418476HCID 178418476, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
85 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-79222293d2ca422582a2e4ede6183025
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928140B2

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