Dimethylformamide → HCID 59832279, compound

HRID 269496Notes

Reaction equation

HRID 269496 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 59832279HCID 59832279, compoundYield 34%

Reagents, catalysts & solvents 1

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

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-55ee2ac8bb974d1599e6e308961d46f0
Source dataset
uspto-grants-2008_11
Patent number
US07446199B2

Reaction notes

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