Bromine → 3-Bromo-2-methylindolizine-6-carbonitrile

HRID 402886

反応式

HRID 402886 の反応式
[Br:1]Br.[CH3:3][C:4]1[CH:5]=[C:6]2[N:11]([CH:12]=1)[CH:10]=[C:9]([C:13]#[N:14])[CH:8]=[CH:7]2>CN(C)C=O.CCOC(C)=O.C([O-])(O)=O.[Na+]>[Br:1][C:12]1[N:11]2[C:6]([CH:7]=[CH:8][C:9]([C:13]#[N:14])=[CH:10]2)=[CH:5][C:4]=1[CH3:3]

参加物

6

反応物 2

HCID 24408BromineHCID 5933682-Methylindolizine-6-carbonitrile

生成物 1

HCID 591920153-Bromo-2-methylindolizine-6-carbonitrile収率 66.5%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
80 °C

実験手順

A solution of bromine (0.33 ml, 6.40 mmol. 1.0 equiv) in 10 ml of N,N-dimethylformamide is added under an atmosphere of argon at 0° C. to a solution of 2-methyl-indolizine-6-carbonitrile (1.0 g, 6.40 mmol) in 5 ml of N,N-dimethylformamide. The reaction mixture is heated in a microwave for 3 minutes at 80° C. After cooling, the reaction mixture is diluted with EtOAc and concentrated aqueous NaHCO3 solution. The aqueous phase is extracted three times with EtOAc. The combined organic layers are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the residue via flash chromatography (hexane/EtOAc 4:1, +0.2% NEt3) affords the title compound (1.0 g, 53%). 1H NMR (400 MHz, d6-DMSO): δ=8.97 (t, J=1.4 Hz, 1H), 7.56 (s, 1H), 7.28 (d, J=9.3 Hz, 1H), 6.87 (dd, J=9.3/1.5 Hz, 1H), 2.15 (d, J=1.0 Hz, 3H). MS (ES+): 236 (M+H)+.

後処理

  1. temperatureAfter cooling
  2. extractionThe aqueous phase is extracted three times with EtOAc
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue via flash chromatography (hexane/EtOAc 4:1, +0.2% NEt3)

出典と根拠

ORDレコード
ord-ab9c98113f544ff5ba71096acba36bb1
出典データセット
uspto-grants-2014_06
特許番号
US08742132B2

関連ノート

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