Cesium carbonate → HCID 58015504、化合物

HRID 219277

反応式

HRID 219277 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:15][C:16]1[C:21]([F:22])=[CH:20][C:19](B2OC(C)(C)C(C)(C)O2)=[CH:18][N:17]=1>O1CCOCC1.O>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([C:19]2[CH:20]=[C:21]([F:22])[C:16]([F:15])=[N:17][CH:18]=2)=[N:3][CH:4]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 8170982-Bromo-5-chloropyridineHCID 533983942,3-Difluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

生成物 1

HCID 58015504HCID 58015504、化合物収率 68%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

To a pressure vessel was added 2-bromo-5-chloropyridine (3.0 g, 16 mmol), cesium carbonate (15 g, 47 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(ii) dichloride dichloromethane complex (2.5 g, 3.1 mmol), and 2,3-difluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (4.5 g, 19 mmol) in 1,4-dioxane (120 mL) and water (22 mL). The mixture was flushed with argon, sealed and stirred at 90° C. for three hours. The mixture was concentrated, diluted with dichloromethane and washed with water. Organic extracts were concentrated and purified by MPLC (eluted with 0-10% methanol in dichloromethane) to yield 5-(5-chloropyridin-2-yl)-2,3-difluoropyridine as a yellow solid (2.4 g, 68%). MS m/z=227.2 [M+1]+. Calc'd for C10H5ClF2N2: 226.6.

後処理

  1. customThe mixture was flushed with argon
  2. customsealed
  3. concentrationThe mixture was concentrated
  4. additiondiluted with dichloromethane
  5. washwashed with water
  6. concentrationOrganic extracts were concentrated
  7. custompurified by MPLC (eluted with 0-10% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-c476fa2be4e1426985ea097a6e796db4
出典データセット
uspto-grants-2012_06
特許番号
US08198448B2

関連ノート

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