Methylamine → 3-bromo-6-methyl-5H,6H,7H-pyrrolo[3,4-b]pyridin-7-one

HRID 216981

반응식

HRID 216981 반응식
[CH3:1][NH2:2].[Br:3][C:4]1[CH:5]=[C:6]([CH2:14]Br)[C:7]([C:10](OC)=[O:11])=[N:8][CH:9]=1>O1CCCC1>[Br:3][C:4]1[CH:5]=[C:6]2[CH2:14][N:2]([CH3:1])[C:10](=[O:11])[C:7]2=[N:8][CH:9]=1

참가 물질

4

반응물 2

HCID 6329MethylamineHCID 58171990Methyl 5-bromo-3-(bromomethyl)pyridine-2-carboxylate

생성물 1

HCID 595685813-bromo-6-methyl-5H,6H,7H-pyrrolo[3,4-b]pyridin-7-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

Methylamine (2M in THF, 9.05 mL) was added to methyl 5-bromo-3-(bromomethyl)picolinate (Example 32, step (i), 1.036 g) in tetrahydrofuran (5 mL) at 20° C. under nitrogen. The resulting suspension was stirred at 70° C. for 30 min. The reaction mixture was cooled and filtered, and the filtrate evaporated to dryness to afford crude product. The crude product was purified by chromatography on silica eluting with ethyl acetate/dichloromethane (5:95 to 100:0). The solid collected during the filtration was dissolved in ethyl acetate and washed with water, extracted with dichloromethane, and then washed with saturated aqueous sodium bicarbonate solution and extracted again with dichloromethane. The combined organic extracts were dried over magnesium sulfate, and then combined with the chromatographed material to afford the sub-titled compound (0.372 g).

후처리

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. customthe filtrate evaporated to dryness
  4. customto afford crude product
  5. customThe crude product was purified by chromatography on silica eluting with ethyl acetate/dichloromethane (5:95 to 100:0)
  6. filtrationThe solid collected during the filtration
  7. dissolutionwas dissolved in ethyl acetate
  8. washwashed with water
  9. extractionextracted with dichloromethane
  10. washwashed with saturated aqueous sodium bicarbonate solution
  11. extractionextracted again with dichloromethane
  12. dry with materialThe combined organic extracts were dried over magnesium sulfate

출처 및 근거

ORD 기록
ord-9e012ff2f8a64f07aa3e9c7fbc2587ef
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193239B2

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