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Bromide ion → 3-Bromo-6-({[4-(methyloxy)phenyl]methyl}oxy)pyrido[2,3-b]pyrazine

HRID 657074
ノート
印刷プレビュー

反応式

HRID 657074 の反応式
FC(F)(F)S(O[C:7]1[N:12]=[C:11]2[N:13]=[C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH:15]=[CH:16][C:10]2=[N:9][CH:8]=1)(=O)=O.[Br-:29]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:29][C:7]1[N:12]=[C:11]2[N:13]=[C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH:15]=[CH:16][C:10]2=[N:9][CH:8]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 259Bromide ionHCID 594373856-({[4-(Methyloxy)phenyl]methyl}oxy)pyrido[2,3-b]pyrazin-3-yl trifluoromethanesulfonate

生成物 1

HCID 594373343-Bromo-6-({[4-(methyloxy)phenyl]methyl}oxy)pyrido[2,3-b]pyrazine収率 102.6%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒2 回HCID 1140Toluene溶媒

反応条件

温度
85 °C

実験手順

6-({[4-(Methyloxy)phenyl]methyl}oxy)pyrido[2,3-b]pyrazin-3-yl trifluoromethanesulfonate (1.39 g, 3.35 mmol) was dissolved in dry toluene (100 mL) under argon and tetrabutylammonium bromide (2.16 g, 6.7 mmol) was added. The reaction was heated at 85° C. for 4 h; 1.08 g of tetrabutylammonium bromide were added and the reaction was heated at 90° C. for another 6 h; 0.54 g of bromide were added and the reaction was heated for 3 h. The reaction was cooled to rt, the toluene was evaporated, the residue was partitioned between water (200 mL) and diethyl ether (400 mL). The layers were separated and the aqueous was extracted with diethyl ether (2×300 mL). The organic phases were combined and washed with water (300 mL) then dried and evaporated to afford the title compound (1.19 g, 100%).

後処理

  1. temperaturethe reaction was heated at 90° C. for another 6 h
  2. temperaturethe reaction was heated for 3 h
  3. temperatureThe reaction was cooled to rt
  4. customthe toluene was evaporated
  5. customthe residue was partitioned between water (200 mL) and diethyl ether (400 mL)
  6. customThe layers were separated
  7. extractionthe aqueous was extracted with diethyl ether (2×300 mL)
  8. washwashed with water (300 mL)
  9. customthen dried
  10. customevaporated

出典と根拠

ORDレコード
ord-427e1569a9744b768318dc4b9068bd4b
出典データセット
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08071592B2

反応ノート

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