Nitrogen → HCID 68000588、化合物

HRID 932187

反応式

HRID 932187 の反応式
Br[C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:5]=[CH:4][CH:3]=1.N#N.[Br-].[CH2:16]([Zn+])[CH2:17][CH3:18]>C1COCC1.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>[CH2:16]([C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:5]=[CH:4][CH:3]=1)[CH2:17][CH3:18]

参加物

6

反応物 3

HCID 947NitrogenHCID 2758810Ethyl 6-BromopicolinateHCID 178455869HCID 178455869、化合物

生成物 1

HCID 68000588HCID 68000588、化合物

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of ethyl 6-bromopicolinate (8 g, 34.8 mmol, purchased from AK Scientific, Inc., Union City, Calif.) in THF (200 mL) was sparged with N2 at 0° C. for 20 min. To the mixture under N2 atmosphere was added Pd(PPh3)4 (3.21 g, 2.78 mmol) and a solution of propylzinc bromide (100 mL, 0.5 M in THF, 50.0 mmol) dropwise over 30 min. The mixture was removed from the ice bath and heated to reflux for 18 h. After that time the solution was cooled to rt, poured into saturated aqueous NH4Cl solution (18 mL), diluted with water (30 mL), and extracted with EtOAc (3×30 mL). The combined organic layers were washed with water and sat. aq. NaCl solution and were dried over Na2SO4. After removal of the organic solvents under reduced pressure, purification of the residue by flash chromatography on silica gel with 0 to 50% EtOAc/hexanes provided the title compound. Mass Spectrum (ESI) m/z=194.0 (M+1).

後処理

  1. customThe mixture was removed from the ice bath
  2. temperatureheated
  3. temperatureto reflux for 18 h
  4. additionpoured into saturated aqueous NH4Cl solution (18 mL)
  5. additiondiluted with water (30 mL)
  6. extractionextracted with EtOAc (3×30 mL)
  7. washThe combined organic layers were washed with water and sat. aq. NaCl solution
  8. dry with materialwere dried over Na2SO4
  9. customAfter removal of the organic solvents
  10. customunder reduced pressure, purification of the residue by flash chromatography on silica gel with 0 to 50% EtOAc/hexanes

出典と根拠

ORDレコード
ord-541c9da75e474d679879c8dbe060a92e
出典データセット
uspto-grants-2016_03
特許番号
US09296736B2

関連ノート

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