Potassium Carbonate → HCID 86658616, 화합물

HRID 1517000노트

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HRID 1517000 반응식
[Cl:1][C:2]1[C:7]([N:8]=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[C:6](I)[CH:5]=[CH:4][N:3]=1.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>COCCOC.[Pd].P.P.P.P>[Cl:1][C:2]1[C:7]([NH2:8])=[C:6]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[O:30][CH3:29])[CH:5]=[CH:4][N:3]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 58479601HCID 58479601, 화합물

생성물 1

HCID 86658616HCID 86658616, 화합물수율 78.3%

시약·촉매·용매 2

HCID 86658617HCID 86658617, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

2-chloro-4-iodo-N-(triphenylphosphoranylidene) pyridin-3-amine (12 g, 23 mmol), (2-methoxyphenyl) boronic acid (4.25 g, 28 mmol), 2M potassium carbonate solution (46.6 ml, 93 mmol) were poured in 120 mL DME and degassed with bubbling nitrogen for 15 min. To the stirred solution was added tetrakisphosphine palladium(0) (1.35 g, 1.12 mmol) and reaction mixture was degassed for another 10 min. Reaction mixture was then refluxed for 48 h. Cooled reaction mixture was partitioned between ethyl acetate and brine. Organic layer was isolated, dried over anhd. Na2SO4 and purified by silica gel column chromatography using 5-30% ethyl acetate/hexanes as eluent. 2-chloro-4-(2-methoxyphenyl)pyridin-3-amine (4.3 g, 18 mmol, 78% yield) was isolated as liquid oil which turns into white crystals upon standing at room temperature.

후처리

  1. customdegassed with bubbling nitrogen for 15 min
  2. additionTo the stirred solution was added
  3. customwas degassed for another 10 min
  4. customReaction mixture
  5. temperaturewas then refluxed for 48 h
  6. temperatureCooled
  7. customreaction mixture
  8. customwas partitioned between ethyl acetate and brine
  9. customOrganic layer was isolated
  10. customdried over anhd
  11. customNa2SO4 and purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-40bbc5aaf6b64f6aad46ddabc68ad8f9
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227801B2

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