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

HRID 216667

반응식

HRID 216667 반응식
[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]

참가 물질

6

반응물 2

HCID 24408BromineHCID 5933682-Methylindolizine-6-carbonitrile

생성물 1

HCID 591920153-Bromo-2-methylindolizine-6-carbonitrile수율 66.5%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
80 °C

실험 절차

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)30.

후처리

  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)

출처 및 근거

ORD 기록
ord-e5602914663c4050abe47d36fca8998f
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193236B2

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