Methanol → 7-Bromo-2-methylsulfanyl-5-(2-trimethylsilanyl-ethoxymethoxy)-pyrrolo[2,1-f][1,2,4]triazine

HRID 1262333Notes

Reaction equation

HRID 1262333 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]2=[C:9]([O:12][CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:10]=[CH:11][N:5]2[N:4]=1.CO.[Br:23]N1C(=O)CCC1=O>C1COCC1>[Br:23][C:11]1[N:5]2[C:6]([CH:7]=[N:8][C:3]([S:2][CH3:1])=[N:4]2)=[C:9]([O:12][CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:19])([CH3:18])[CH3:20])[CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 67184N-bromobutanimideHCID 667125552-Methylsulfanyl-5-(2-trimethylsilanyl-ethoxymethoxy)-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 667122877-Bromo-2-methylsulfanyl-5-(2-trimethylsilanyl-ethoxymethoxy)-pyrrolo[2,1-f][1,2,4]triazineYield 83.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into a 1-Neck round-bottom flask, 2-Methylsulfanyl-5-(2-trimethylsilanyl-ethoxymethoxy)-pyrrolo[2,1-f][1,2,4]triazine (1.05 g, 3.37 mmol), Tetrahydrofuran (50 mL) and Methanol (25 mL) were added and stirred at room temperature. N-Bromosuccinimide (0.630 g, 3.54 mmol) in THF (20 mL) was added to the reaction mixture . The reaction was stirred at room temperature for 2 hours. LCMS suggested no SM. The solvent was removed under vacuum. The reaction was partitioned with water and Et2O. The organic was separated, washed with Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The solvent was removed under vacuum. The reaction mixture was purified via ISCO column chromatography with hexane and EtOAc as eluant (5 to 20% EtOAc). The collected fractions afforded 7-Bromo-2-methylsulfanyl-5-(2-trimethylsilanyl-ethoxymethoxy)-pyrrolo[2,1-f][1,2,4]triazine as an oil (1.10 g, 83%).

Workup

  1. stirringThe reaction was stirred at room temperature for 2 hours
  2. customThe solvent was removed under vacuum
  3. customThe reaction was partitioned with water and Et2O
  4. customThe organic was separated
  5. washwashed with Brine
  6. dry with materialdried over Na2SO4
  7. filtrationThe solid was filtered
  8. washwashed with DCM
  9. customThe solvent was removed under vacuum
  10. customThe reaction mixture was purified via ISCO column chromatography with hexane and EtOAc as eluant (5 to 20% EtOAc)

Sources & evidence

ORD record
ord-00f4546f3ee841908e4622b3a3eb5204
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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