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Cesium carbonate → ethyl 2-(diphenylmethyleneamino)-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate

HRID 1506400
Notes
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Reaction equation

HRID 1506400 reaction equation
[C:1]1([C:7](=[N:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:27]1([N:33]2[C:37]([C:38]([F:41])([F:40])[F:39])=[C:36]([C:42]3[O:46][N:45]=[C:44]4[C:47]5[C:52]([CH2:53][CH2:54][C:43]=34)=[CH:51][C:50]([CH:55]=[CH2:56])=[CH:49][CH:48]=5)[CH:35]=[N:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CS(C)=O>[C:1]1([C:7](=[N:14][CH:15]([CH2:56][CH2:55][C:50]2[CH:51]=[C:52]3[C:47](=[CH:48][CH:49]=2)[C:44]2=[N:45][O:46][C:42]([C:36]4[CH:35]=[N:34][N:33]([C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=5)[C:37]=4[C:38]([F:40])([F:41])[F:39])=[C:43]2[CH2:54][CH2:53]3)[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 671704203-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole

Product 1

HCID 86669896ethyl 2-(diphenylmethyleneamino)-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoateYield 97%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of ethyl 2-(diphenylmethyleneamino)acetate (315 mg, 1.178 mmol) in anhydrous dimethylsulfoxide (1 mL) was purged with nitrogen for 10 min before cesium carbonate (192 mg, 0.589 mmol) was added. The mixture was purged with nitrogen for 5 min. and stirred at room temperature for 30 min. Next, 3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole (Preparation 50A, 100 mg, 0.245 mmol) was added, the mixture was purged with nitrogen for 5 min and then stirred at 40° C. for 5 hr. The reaction mixture was cooled, diluted with water (10 mL), and extracted with ethyl acetate (3×5 mL). The ethyl acetate extracts were dried over sodium sulfate and concentrated under reduced pressure. Flash chromatography purification using an ISCO setup (4 g silica gel column, 10→100% ethyl acetate in hexanes) afforded ethyl 2-(diphenylmethyleneamino)-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate (160 mg, 0.237 mmol, 97% yield) as a glassy solid. LC/MS M+1=675.4.

Workup

  1. additionwas added
  2. customThe mixture was purged with nitrogen for 5 min.
  3. customthe mixture was purged with nitrogen for 5 min
  4. stirringstirred at 40° C. for 5 hr
  5. temperatureThe reaction mixture was cooled
  6. additiondiluted with water (10 mL)
  7. extractionextracted with ethyl acetate (3×5 mL)
  8. dry with materialThe ethyl acetate extracts were dried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customFlash chromatography purification

Sources & evidence

ORD record
ord-001b29163840478499f508e0c39035b6
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09216972B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes