Sodium Bicarbonate → 5-Chloro-1,3-dihydro-2H-pyrrolo[2,3-c]pyridin-2-one

HRID 2394335노트

반응식

HRID 2394335 반응식
N[C:2]1[C:3]([CH2:9][C:10]#[N:11])=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.C([O-])(O)=[O:13].[Na+]>Cl>[Cl:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][N:6]=1)[NH:11][C:10](=[O:13])[CH2:9]2

참가 물질

4

반응물 2

HCID 516892Sodium BicarbonateHCID 18973056HCID 18973056, 화합물

생성물 1

HCID 189730325-Chloro-1,3-dihydro-2H-pyrrolo[2,3-c]pyridin-2-one수율 46%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

(5-Amino-2-chloro-4-pyridyl)acetonitrile (1.40 g, 8.4 mmol) was taken up in 6N HCl solution (100 mL) and heated between 50° and 100° C. for 2 hours. After cooling, the solution was adjusted to pH 7 by addition of solid NaHCO3 and extracted with ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was subjected to flash chromatography on silica gel using ethyl acetate as eluant. (Some methanol was used to help dissolve the solid). Fractions containing the desired product were combined and concentrated to leave the title compound as a solid (650 mg, 46%), m.p. 230° C. (dec.) The NMR spectrum indicated that this material contained a small amount of the by-product, 2-amino-5-chloro-6-azaindole in addition to the title compound. Nonetheless, this material was used in the next step without further purification.

후처리

  1. temperatureheated between 50° and 100° C. for 2 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe combined ethyl acetate extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. dissolutionto help dissolve the solid)
  8. additionFractions containing the desired product
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-23844943d8244458a3483e8e1cb172c2
출처 데이터셋
uspto-grants-1998_09
특허 번호
US05811432

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