Sodium Carbonate → 6-Fluoro-3,4-dimethoxy-2-(2-pyridyl)benzonitrile

HRID 1582379노트

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HRID 1582379 반응식
[F:1][C:2]1[C:7]([C:8]#[N:9])=[C:6](I)[C:5]([O:11][CH3:12])=[C:4]([O:13][CH3:14])[CH:3]=1.B([O-])O[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I.O.C(OCC)(=O)C.O1CCOCC1>[F:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[C:5]([O:11][CH3:12])=[C:4]([O:13][CH3:14])[CH:3]=1

참가 물질

10

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 227212146-Fluoro-2-iodo-3,4-dimethoxybenzonitrileHCID 178514833HCID 178514833, 화합물

생성물 1

HCID 98138056-Fluoro-3,4-dimethoxy-2-(2-pyridyl)benzonitrile수율 48%

시약·촉매·용매 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

Stirred dioxane (20 ml) at 80° C. was charged with 6-fluoro-2-iodo-3,4-dimethoxybenzonitrile from Example 1(a) (1.0 g, 3.3 mmol), tetrakis(triphenylphosphine)palladium(0) (0.19 g, 0.16 mmol), the pyridyl boronate from step (a) above (6.1 g, estimated to be 9.9 mmol), copper(I)iodide (0.25 g, 1.3 mmol), sodium carbonate (0.69 g, 6.5 mmol) and triphenylphosphine (0.17 g, 0.65 mmol) and the resulting brown slurry heated to reflux and stirred at this temperature overnight. The resulting suspension was cooled to room temperature, ethyl acetate (20 ml) and water (10 ml) added and the resulting mixture filtered through Arbocel™ filter aid. The phases were separated and the aqueous phase extracted with ethyl acetate (2×20 ml). The organic phases were combined, washed with saturated aqueous NaCl and stripped to an oil. Acetonitrile was added and the mixture warmed then cooled. The resulting suspension was filtered to give a solid that was dried in vacuo overnight at 45° C. to give 0.419 of the product (48%).

후처리

  1. temperatureto reflux
  2. filtrationthe resulting mixture filtered through Arbocel™
  3. filtrationfilter aid
  4. customThe phases were separated
  5. extractionthe aqueous phase extracted with ethyl acetate (2×20 ml)
  6. washwashed with saturated aqueous NaCl
  7. additionAcetonitrile was added
  8. temperaturethe mixture warmed
  9. temperaturethen cooled
  10. filtrationThe resulting suspension was filtered
  11. customto give a solid
  12. customthat was dried in vacuo overnight at 45° C.

출처 및 근거

ORD 기록
ord-b95961a7c2bb411b993ce02ce68a7f5e
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06734303B2

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