Potassium Phosphate, Tribasic → (E)-methyl 4-(5-(2-ethoxyvinyl)-4-methylthiazol-2-yl)-1-methyl-1H-pyrazole-5-carboxylate

HRID 60145

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HRID 60145 반응식
[CH2:1]([O:3]/[CH:4]=[CH:5]/B1OC(C)(C)C(C)(C)O1)[CH3:2].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.Br[C:53]1[S:57][C:56]([C:58]2[CH:59]=[N:60][N:61]([CH3:67])[C:62]=2[C:63]([O:65][CH3:66])=[O:64])=[N:55][C:54]=1[CH3:68].C(=O)([O-])O.[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.C(#N)C.O>[CH2:4]([O:3]/[CH:1]=[CH:2]/[C:53]1[S:57][C:56]([C:58]2[CH:59]=[N:60][N:61]([CH3:67])[C:62]=2[C:63]([O:65][CH3:66])=[O:64])=[N:55][C:54]=1[CH3:68])[CH3:5]

참가 물질

10

반응물 5

HCID 62657Potassium Phosphate, TribasicHCID 516892Sodium BicarbonateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 219739081-Ethoxyethene-2-boronic acid pinacol esterHCID 90383445methyl 4-(5-bromo-4-methylthiazol-2-yl)-1-methyl-1H-pyrazole-5-carboxylate

생성물 1

HCID 90383511(E)-methyl 4-(5-(2-ethoxyvinyl)-4-methylthiazol-2-yl)-1-methyl-1H-pyrazole-5-carboxylate수율 63.8%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

(E)-2-(2-ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (63 mg), palladium acetate (7.1 mg), tripotassium phosphate (67 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (26 mg), and water (0.35 ml) were added to an acetonitrile (4.0 ml) solution of the methyl 4-(5-bromo-4-methylthiazol-2-yl)-1-methyl-1H-pyrazole-5-carboxylate (50 mg) obtained in (Example 5.11) <Step 1>, and the obtained mixture was then stirred under heating in a nitrogen atmosphere for 2 hours at 90° C. Thereafter, ethyl acetate (50 ml) and a saturated sodium hydrogen carbonate aqueous solution (30 ml) were added to the reaction solution. After extraction of organic layers, water layers were extracted with ethyl acetate (50 ml). The organic layers were combined. The combined organic layer was washed with a saturated saline, and was then dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the obtained residue was then purified by silica gel column chromatography (silica gel: eluent; heptane:ethyl acetate=92:8-40:60), so as to obtain the title compound (31 mg) in the form of a yellow solid.

후처리

  1. customobtained in (Example 5.11) <Step 1>
  2. extractionAfter extraction of organic layers, water layers
  3. extractionwere extracted with ethyl acetate (50 ml)
  4. washThe combined organic layer was washed with a saturated saline
  5. dry with materialwas then dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled away under reduced pressure
  7. customthe obtained residue was then purified by silica gel column chromatography (silica gel: eluent; heptane:ethyl acetate=92:8-40:60)

출처 및 근거

ORD 기록
ord-8adc4bd725a3487796553da0eed739c8
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440970B2

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