Potassium vinyltrifluoroborate → methyl 4-(4-(difluoromethyl)-5-vinylthiazol-2-yl)-1-methyl-1H-pyrazole-5-carboxylate

HRID 60143

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HRID 60143 반응식
F[C:2](OB([O-])[O-])=[C:3]([F:5])[F:4].[K+].[K+].Br[C:13]1[S:17][C:16]([C:18]2[CH:19]=[N:20][N:21]([CH3:27])[C:22]=2[C:23]([O:25][CH3:26])=[O:24])=[N:15][C:14]=1[CH:28](F)F.[B-](F)(F)(F)C=C.[K+]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(OCC)(=O)C.C(N(CC)CC)C.C(O)C>[F:4][CH:3]([F:5])[C:2]1[N:15]=[C:16]([C:18]2[CH:19]=[N:20][N:21]([CH3:27])[C:22]=2[C:23]([O:25][CH3:26])=[O:24])[S:17][C:13]=1[CH:14]=[CH2:28]

참가 물질

8

반응물 3

HCID 23679353Potassium vinyltrifluoroborateHCID 86620274Potassium trifluorovinylborateHCID 90383233methyl 4-(5-bromo-4-(difluoromethyl)thiazol-2-yl)-1-methyl-1H-pyrazole-5-carboxylate

생성물 1

HCID 117761094methyl 4-(4-(difluoromethyl)-5-vinylthiazol-2-yl)-1-methyl-1H-pyrazole-5-carboxylate수율 58%

시약·촉매·용매 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매2회HCID 702Ethanol용매HCID 8471Triethylamine용매2회HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

Potassium trifluorovinylborate (172 mg), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (31 mg), and triethylamine (59.4 μl) were added to an ethanol (2.1 ml) solution of the methyl 4-(5-bromo-4-(difluoromethyl)thiazol-2-yl)-1-methyl-1H-pyrazole-5-carboxylate (150 mg) obtained in (Example 1.4) <Step 1>, and the obtained mixture was then stirred in a nitrogen atmosphere at 100° C. for 17 hours. Thereafter, potassium trifluoro(vinyl)borate (342 mg), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (62 mg), and triethylamine (59.4 μl) were added to the reaction solution, and the obtained mixture was stirred again in a nitrogen atmosphere at 100° C. for 2 hours 40 minutes. Thereafter, ethyl acetate (100 ml) and a saturated saline (50 ml) were added to the reaction solution. An organic layer was extracted, 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=95:5-50:50), so as to obtain the title compound (74 mg) in the form of a colorless solid.

후처리

  1. customobtained in (Example 1.4) <Step 1>
  2. stirringthe obtained mixture was stirred again in a nitrogen atmosphere at 100° C. for 2 hours 40 minutes
  3. extractionAn organic layer was extracted
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled away under reduced pressure
  6. customthe obtained residue was then purified by silica gel column chromatography (silica gel:eluent; heptane:ethyl acetate=95:5-50:50)

출처 및 근거

ORD 기록
ord-f7e2c1a181be472c8a441820e6365940
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440970B2

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