Selenium Dioxide → 4-Chloro-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carboxylic acid methyl ester

HRID 60256노트

반응식

HRID 60256 반응식
[CH3:1][O:2][C:3]([CH:5]1[NH:13][CH2:12][C:11]2[NH:10][C:9]3[N:14]=[CH:15][CH:16]=[C:17]([Cl:18])[C:8]=3[C:7]=2[CH2:6]1)=[O:4].[Se](=O)=O>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[N:13]=[CH:12][C:11]2[NH:10][C:9]3[N:14]=[CH:15][CH:16]=[C:17]([Cl:18])[C:8]=3[C:7]=2[CH:6]=1)=[O:4]

참가 물질

4

반응물 2

HCID 24007Selenium DioxideHCID 583650474-Chloro-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carboxylic acid methyl ester

생성물 1

HCID 583649684-Chloro-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carboxylic acid methyl ester

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

A mixture of 4-chloro-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carboxylic acid methyl ester (2.1 g, 7.9 mmol) and selenium dioxide (1.20 g, 11.1 mol) in 1,4-dioxane (50 mL) was heated at 100° C. for 3.5 hours. The resulting grey slurry was filtered whilst hot through a pad of celite and the pad washed with hot THF and 25% methanol in dichloromethane. The combined filtrate was concentrated in-vacuo and the resultant residue triturated with methanol (10 mL). The resultant solid was collected by filtration and left to air dry to afford the title compound as an off white solid (1.03 g, 48%). 1H NMR (400 MHz, DMSO-d6): 13.02 (s, 1H), 9.06 (d, J=1.1 Hz, 1H), 8.94 (d, J=1.0 Hz, 1H), 8.63 (d, J=5.3 Hz, 1H), 7.54 (d, J=5.3 Hz, 1H), 3.93 (s, 3H).

후처리

  1. filtrationThe resulting grey slurry was filtered whilst hot through a pad of celite
  2. washthe pad washed with hot THF and 25% methanol in dichloromethane
  3. concentrationThe combined filtrate was concentrated in-vacuo
  4. customthe resultant residue triturated with methanol (10 mL)
  5. filtrationThe resultant solid was collected by filtration
  6. waitleft to air
  7. customdry

출처 및 근거

ORD 기록
ord-ad7969c9339a4e38bd36216aa11d49c9
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440976B2

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