Dimethylformamide → HCID 59832279, 화합물

HRID 269496노트

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HRID 269496 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 59832279HCID 59832279, 화합물수율 34%

시약·촉매·용매 1

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

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-55ee2ac8bb974d1599e6e308961d46f0
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446199B2

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