Potassium Carbonate → HCID 86658616、化合物

HRID 1517000ノート

反応式

HRID 1517000 の反応式
[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

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 58479601HCID 58479601、化合物

生成物 1

HCID 86658616HCID 86658616、化合物収率 78.3%

試薬・触媒・溶媒 2

HCID 86658617HCID 86658617、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-40bbc5aaf6b64f6aad46ddabc68ad8f9
出典データセット
uspto-grants-2012_07
特許番号
US08227801B2

反応ノート

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