Sodium Carbonate → 2-Chloro-2'-fluoro-3,4'-bipyridine

HRID 446296ノート

反応式

HRID 446296 の反応式
[F:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[C:15](B(O)O)=[CH:14][CH:13]=[CH:12][N:11]=1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].O>[Cl:9][C:10]1[C:15]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([F:1])[CH:7]=2)=[CH:14][CH:13]=[CH:12][N:11]=1

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 2762704(2-Chloropyridin-3-yl)boronic acidHCID 70235702-Fluoro-4-iodopyridine

生成物 1

HCID 161089822-Chloro-2'-fluoro-3,4'-bipyridine

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To 2-fluoro-4-iodopyridine (9.45 g, 42.4 mmol), 2-chloropyridine-3-boronic acid (10.0 g, 63.5 mmol), Na2CO3 (13.5 g, 127 mmol), Pd(OAc)2 (480 mg, 2.12 mmol) and P(tBu)3·HBF4 (1.23 g, 4.24 mmol) was added dioxane (125 mL) and water (45 mL). The mixture was heated overnight at 100° C. in a sealed tube. The resulting mixture was diluted with EtOAc and extracted with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The resulting solid was triturated with n-Hexanes and dried to yield 2-chloro-2′-fluoro-[3,4′]bipyridinyl. MS m/z=209 [M+1]+. Calc'd for C10H6ClFN2: 208.62.

後処理

  1. extractionextracted with water and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting solid was triturated with n-Hexanes
  6. customdried

出典と根拠

ORDレコード
ord-b3b27f8b34844ed1bfd5c71575bd6836
出典データセット
uspto-grants-2013_07
特許番号
US08476434B2

反応ノート

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