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

HRID 227743ノート

反応式

HRID 227743 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+].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.[H+].[B-](F)(F)(F)F>CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].O.O1CCOCC1>[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

10

反応物 5

HCID 10340Sodium CarbonateHCID 28118Tetrafluoroboric acidHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 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 4

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane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 C10H6CiFN2: 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-d2d3edd44f474d3886b6c242978844df
出典データセット
uspto-grants-2009_07
特許番号
US07560551B2

反応ノート

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