Phenol → (S)-tert-Butyl (1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)-3-phenoxypropyl)carbamate

HRID 1052371Notes

Reaction equation

HRID 1052371 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:15][CH2:16][C@H:17]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[C:18]1[N:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:22](=[O:30])[C:21]2=[CH:31][CH:32]=[CH:33][N:20]2[N:19]=1.[I-].[K+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[O:30]=[C:22]1[C:21]2=[CH:31][CH:32]=[CH:33][N:20]2[N:19]=[C:18]([C@@H:17]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:38])[CH3:39])[CH2:16][CH2:15][O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:23]1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 5

HCID 996PhenolHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 131736118(S)-tert-Butyl (3-bromo-1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamate

Product 1

HCID 131736119(S)-tert-Butyl (1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)-3-phenoxypropyl)carbamateYield 57.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Phenol (6 mg, 0.06 mmol) was dissolved in 450 μl of N,N-dimethylformamide. Potassium carbonate (6 mg, 0.05 mmol) was added and the reaction was stirred at room temperature for 30 min. (S)-tert-Butyl (3-bromo-1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamate (45 mg, 0.03 mmol) and potassium iodide (1 mg, 0.001 mmol) were added and the reaction was heated at 70° C. for 3 h. The mixture was poured into a 4% aqueous sodium bicarbonate and extracted with ethyl acetate. The combined organic phases were washed with water, brine, dried over sodium sulphate and evaporated under reduced pressure. The crude was purified by SP1® Purification System (0% to 50%, hexane-ethyl acetate) to give 8 mg (57% yield) of the title compound. Purity 98%.

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases were washed with water, brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated under reduced pressure
  6. customThe crude was purified by SP1® Purification System (0% to 50%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-54c1c8051f1a48019952c9391bd277db
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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