Sodium Carbonate → 3-Bromo-5-(3-(trifluoromethyl)phenyl)pyridine

HRID 2117260노트

반응식

HRID 2117260 반응식
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[F:9][C:10]([F:21])([F:20])[C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>CCO.O.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:10]([F:21])([F:20])[F:9])[CH:16]=2)[CH:7]=1

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 693693,5-DibromopyridineHCID 27343883-(Trifluoromethyl)phenylboronic acid

생성물 1

HCID 299195683-Bromo-5-(3-(trifluoromethyl)phenyl)pyridine수율 26.5%

시약·촉매·용매 4

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 702Ethanol용매HCID 962Water용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

A mixture of 3,5-dibromopyridine (1.2 g, 5 mmol), 3-trifluoromethylphenyl boronic acid (0.95 g, 5 mmol), tetrakis(triphenylphosphine)palladium (0) (0.23 g, 0.2 mmol), and sodium carbonate (1.1 g, 10 mmol) in EtOH (10 mL) and water (1 mL) were heated in an oil bath at 70° C. for 3 days. The mixture was cooled to RT and diluted with EtOAc (20 mL) and water (10 mL). The layers were partitioned and the organic layer was dried (Na2SO4), filtered and concentrated. Purification by chromatography (eluting with 10:1 hexanes/EtOAc) resulted in 0.4 g (26%) of the title compound: 1H NMR (CDCl3, 400 MHz) δ 8.76 (d, 1H, J=2.1 Hz), 8.71 (d, 1H, J=2.1 Hz), 8.06 (dd, 1H, J=2.1, 2.1 Hz), 7.80 (s, 1H), 7.74-7.61 (m, 3H); APCI MS m/z 304.0, 302.0 (M+1).

후처리

  1. temperatureThe mixture was cooled to RT
  2. customThe layers were partitioned
  3. dry with materialthe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. washby chromatography (eluting with 10:1 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-7af0c2c5a2ae4c9da13112cd06b5616c
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07442694B2

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