Triethylamine → HCID 58444571, 화합물

HRID 1509767노트

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HRID 1509767 반응식
[CH2:1]([CH:3]1[CH2:8][O:7][CH:6]([C:9]2[CH:14]=[CH:13][C:12](B3OC(C)(C)C(C)(C)O3)=[C:11]([F:24])[CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].Br[C:26]1[CH:31]=[C:30]([F:32])[C:29]([C:33]([F:48])([F:47])[O:34][C:35]2[CH:36]=[C:37]([F:46])[C:38]([C:42]([F:45])([F:44])[F:43])=[C:39]([F:41])[CH:40]=2)=[C:28]([F:49])[CH:27]=1.C(N(CC)CC)C.C(=O)([O-])O.[K+]>C1COCC1.O.CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C.CC(OC)(C)C>[F:41][C:39]1[CH:40]=[C:35]([CH:36]=[C:37]([F:46])[C:38]=1[C:42]([F:43])([F:45])[F:44])[O:34][C:33]([F:47])([F:48])[C:29]1[C:28]([F:49])=[CH:27][C:26]([C:12]2[CH:13]=[CH:14][C:9]([CH:6]3[CH2:5][CH2:4][CH:3]([CH2:1][CH3:2])[CH2:8][O:7]3)=[CH:10][C:11]=2[F:24])=[CH:31][C:30]=1[F:32]

참가 물질

9

반응물 4

HCID 8471TriethylamineHCID 516893Potassium BicarbonateHCID 58444567HCID 58444567, 화합물HCID 58444590HCID 58444590, 화합물

생성물 1

HCID 58444571HCID 58444571, 화합물

시약·촉매·용매 4

HCID 178424406HCID 178424406, 화합물촉매HCID 962Water용매2회HCID 8028Tetrahydrofuran용매HCID 15413tert-Butyl methyl ether용매

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온도
50 °C

실험 절차

5.20 g (15.0 mmol) of 5-ethyl-2-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]tetrahydropyran are initially introduced in 35 ml of THF together with 6.93 g (15.0 mmol) of 5-((4-bromo-2,6-difluorophenyl)-difluoromethoxy)-1,3-difluoro-2-(trifluoromethyl)benzene. 590 mg (0.75 mmol) of bis(tri-o-tolylphosphine)palladium(II) chloride and 0.1 ml (0.75 mmol) of triethylamine are added. The mixture is heated to 50° C., and a solution of 2.41 g (24.0 mmol) of potassium hydrogencarbonate in 15 ml of water is added. After 3 h at this temperature, water and MTBE are added, and the organic phase is separated off. The aqueous phase is washed with MTBE, and the combined organic phases are washed with saturated sodium chloride solution and dried using sodium sulfate. The solution is concentrated to dryness, and the crude product is purified by column chromatography (SiO2, n-heptane:toluene=1:1). The further purification is carried out by recrystallisation from ethanol and n-heptane, giving 2-{4′-[(3,5-difluoro-4-trifluoromethylphenoxy)difluoromethyl]-2,3′,5′-trifluorobiphenyl-4-yl}-5-ethyltetrahydropyran as a colourless solid having an m.p. of 90° C.

후처리

  1. customthe organic phase is separated off
  2. washThe aqueous phase is washed with MTBE
  3. washthe combined organic phases are washed with saturated sodium chloride solution
  4. customdried
  5. concentrationThe solution is concentrated to dryness
  6. customthe crude product is purified by column chromatography (SiO2, n-heptane:toluene=1:1)
  7. customThe further purification
  8. customis carried out by recrystallisation from ethanol and n-heptane

출처 및 근거

ORD 기록
ord-6b6fca11ffde44caa23c7ed1b1b426d8
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08211513B2

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