Cesium carbonate → HCID 58015504, 화합물

HRID 219277

반응식

HRID 219277 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 58015504HCID 58015504, 화합물수율 68%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c476fa2be4e1426985ea097a6e796db4
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198448B2

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