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

HRID 60256ノート

反応式

HRID 60256 の反応式
[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]

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ad7969c9339a4e38bd36216aa11d49c9
出典データセット
uspto-grants-2016_09
特許番号
US09440976B2

反応ノート

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