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

HRID 2117260ノート

反応式

HRID 2117260 の反応式
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

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 702Ethanol溶媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-7af0c2c5a2ae4c9da13112cd06b5616c
出典データセット
uspto-grants-2008_10
特許番号
US07442694B2

反応ノート

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