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

HRID 1407420Notes

Reaction equation

HRID 1407420 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d27c2393be2c4741a4eddb1bda8e0a29
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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