Potassium Phosphate, Tribasic → 5-Cyclopropyl-2-fluoropyridine

HRID 401482노트

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HRID 401482 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[CH:9]1(B(O)O)[CH2:11][CH2:10]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.Cl[Pd-](P(C1CC2CC1CC2)C1CC2CC1CC2)[C-]1C=CC=C1N(C)C.[CH-]1C=CC=C1.[Fe+2]>[CH:9]1([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[N:3][CH:4]=2)[CH2:11][CH2:10]1

참가 물질

6

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 27831685-Bromo-2-fluoropyridine

생성물 1

HCID 576908315-Cyclopropyl-2-fluoropyridine

시약·촉매·용매 2

HCID 178482626HCID 178482626, 화합물촉매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

A mixture of 2-fluoro-5-bromopyridine (1.17 ml, 11.4 mmol), cyclopropylboronic acid (1.47 g, 17.1 mmol) and potassium phosphate (7.26 g, 34.2 mmol) in 1,4-dioxane (20 ml) was stirred under argon atmosphere. Chloro(di-2-norbornylphosphino)(2-dimethylaminoferrocen-1-yl)palladium(II) (67 mg, 0.11 mmol) was added. The reaction mixture was heated at 100° C. under argon atmosphere for 48 hours and then cooled down to room temperature. The crude mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography (ISCO Companion|, 80 g column, 0-10% EtOAc/Petroleum ether) to afford the compound (70:30 mixture product:starting material; 1.55 g).

후처리

  1. temperaturecooled down to room temperature
  2. customThe crude mixture was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica gel by flash column chromatography (ISCO Companion|, 80 g column, 0-10% EtOAc/Petroleum ether)
  8. customto afford the compound (70:30 mixture product:starting material; 1.55 g)

출처 및 근거

ORD 기록
ord-085a84f4b6d2487891d7362e7db87c96
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741931B2

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