1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl furo[3,2-c]pyridine-6-carboxylate

HRID 1072983

反応式

HRID 1072983 の反応式
[C:1]([NH:4][CH:5](P(OC)(OC)=O)[C:6]([O:8][CH3:9])=[O:7])(=O)[CH3:2].C1CCN2C(=NCCC2)CC1.[O:27]1[CH:31]=[CH:30][C:29](C=O)=[C:28]1C=O>C(Cl)(Cl)Cl>[O:27]1[C:31]2[CH:30]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[N:4]=[CH:1][C:2]=2[CH:29]=[CH:28]1

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11746707Methyl 2-acetamido-2-(dimethoxyphosphoryl)acetateHCID 13814199Furan-2,3-dicarbaldehyde

生成物 1

HCID 22047280Methyl furo[3,2-c]pyridine-6-carboxylate収率 82.5%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

Methyl (acetylamino)(dimethoxyphosphoryl)acetate (2.34 g, 9.8 mmol) is dissolved in CHCl3 (40 mL), treated with DBU (1.46 mL, 9.8 mmol), stirred for 5 min then added dropwise to a 0° C. solution of furan-2,3-dicarbaldehyde (1.65 g, 8.9 mmol) in CHCl3 (80 mL). The mixture is stirred for 2.5 h as the cooling bath expires then 5.5 h at RT and finally 24 h at 50° C. The mixture is concentrated in vacuo to a yellow oily-solid (6.66 g). The crude material is chromatographed over a standard 100 g slurry-packed silica gel, eluting with 65% EtOAc/hexane. The appropriate fractions are combined and concentrated in vacuo to afford 1.30 g (82%) of methyl furo[3,2-c]pyridine-6-carboxylate as a yellow solid. MS (EI) m/z: 177 (M+).

後処理

  1. stirringThe mixture is stirred for 2.5 h as the cooling bath
  2. custom5.5 h
  3. customat RT
  4. customfinally 24 h
  5. customat 50° C
  6. concentrationThe mixture is concentrated in vacuo to a yellow oily-solid (6.66 g)
  7. customThe crude material is chromatographed over a standard 100 g slurry-packed silica gel
  8. washeluting with 65% EtOAc/hexane
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-fcefbc1462f44d78a8a1d9d47c30686d
出典データセット
uspto-grants-2005_06
特許番号
US06911543B2

関連ノート

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