1-Bromo-3-methylbutane → 6-(3-methylbutyl)-6H-[1,3]thiazolo[5,4-e]indole-7,8-dione

HRID 1407420노트

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HRID 1407420 반응식
[S:1]1[C:5]2=[C:6]3[C:10](=[CH:11][CH:12]=[C:4]2[N:3]=[CH:2]1)[NH:9][C:8](=[O:13])[C:7]3=[O:14].O1CCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30]>CN(C)C=O>[CH3:30][CH:29]([CH3:31])[CH2:28][CH2:27][N:9]1[C:10]2[C:6](=[C:5]3[S:1][CH:2]=[N:3][C:4]3=[CH:12][CH:11]=2)[C:7](=[O:14])[C:8]1=[O:13]

참가 물질

6

반응물 4

HCID 78911-Bromo-3-methylbutaneHCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 117457566H-thiazolo[5,4-e]indole-7,8-dione

생성물 1

HCID 673588366-(3-methylbutyl)-6H-[1,3]thiazolo[5,4-e]indole-7,8-dione수율 57.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 6H-thiazolo[5,4-e]indole-7,8-dione (2.83 g, 13.9 mmol) in a mixture of anhydrous tetrahydrofuran (120 mL) and N,N-dimethylformamide (80 mL) was added cesium carbonate (23.0 g, 70 mmol) at ambient temperature. The deep purple mixture was stirred for 0.5 h followed by the addition of 1-bromo-3-methylbutane (4.15 mL, 35.0 mmol) in one portion. The mixture was stirred at ambient temperature for 16 h and poured into 800 mL of ice-water and extracted with ethyl acetate. The orange solution was filtered through Celite, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to dryness and the residue was triturated with diethyl ether to afford 6-(3-methylbutyl)-6H-[1,3]thiazolo[5,4-e]indole-7,8-dione (2.2 g, 57%): 1H NMR (300 MHz, CDCl3) δ9.36 (s, 1H), 8.38 (d, J=8.6 Hz, 1H), 7.37 (d, J=8.6 Hz, 1H), 3.77-3.69 (m, 2H), 1.74-1.58 (m, 1H), 1.57-1.47 (m, 2H), 0.94 (d, J=6.5 Hz, 6H).

후처리

  1. stirringThe mixture was stirred at ambient temperature for 16 h
  2. extractionextracted with ethyl acetate
  3. filtrationThe orange solution was filtered through Celite
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo to dryness
  7. customthe residue was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-d27c2393be2c4741a4eddb1bda8e0a29
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916580B2

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