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

HRID 2077516
Notes
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Reaction equation

HRID 2077516 reaction equation
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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 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

Product 2

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

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-79222293d2ca422582a2e4ede6183025
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07928140B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes