Dimethylformamide → HCID 59832279、化合物

HRID 269496ノート

反応式

HRID 269496 の反応式
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8](S(C)(=O)=O)[C:5]2=[N:6][CH:7]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.CN([CH:23]=[O:24])C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N:15]1([C:23]([C:2]2[CH:3]=[C:4]3[CH:10]=[CH:9][NH:8][C:5]3=[N:6][CH:7]=2)=[O:24])[CH2:19][CH2:18][CH2:17][CH2:16]1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 31268PyrrolidineHCID 497588975-Bromo-1-(methanesulfonyl)-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 59832279HCID 59832279、化合物収率 34%

試薬・触媒・溶媒 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒

反応条件

温度
80 °C

実験手順

A mixture of 5-bromo-1-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine (300 mg, 1.1 mmol), PdCl2(dppf) (55 mg, 0.07 mmol), and pyrrolidine (2 mL) in DMF (5 mL) was charged with CO balloon. The system was degassed with vacuum twice before it was heated to 80° C. for 6 h. The solution was cooled and poured into water. The aqueous solution was extracted with ethyl acetate (3×50 mL), the combined organic layers were dried over Na2SO4, and the solvent was removed by vacuum evaporation. The crude product was treated with 6N NaOH in MeOH for 2 h. MeOH was removed by evaporation. The aqueous solution was neutralized with 6N HCl to pH 8 and extracted with ethyl acetate. The combined organic layers were dried over Na2SO4 and the solvent was removed by vacuum evaporation to give a yellow solid (80 mg, 0.37 mmol, 34%), which was used directly for the next step. MS (ES+): m/e=216.1 (M+H); LC: 2.18 min.

後処理

  1. additionwas charged with CO balloon
  2. customThe system was degassed with vacuum twice before it
  3. temperatureThe solution was cooled
  4. additionpoured into water
  5. extractionThe aqueous solution was extracted with ethyl acetate (3×50 mL)
  6. dry with materialthe combined organic layers were dried over Na2SO4
  7. customthe solvent was removed by vacuum evaporation
  8. additionThe crude product was treated with 6N NaOH in MeOH for 2 h
  9. customMeOH was removed by evaporation
  10. extractionextracted with ethyl acetate
  11. dry with materialThe combined organic layers were dried over Na2SO4
  12. customthe solvent was removed by vacuum evaporation

出典と根拠

ORDレコード
ord-55ee2ac8bb974d1599e6e308961d46f0
出典データセット
uspto-grants-2008_11
特許番号
US07446199B2

反応ノート

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