Potassium Carbonate → (S)-tert-Butyl (3-(benzyloxy)-1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamate

HRID 1052394Notes

Reaction equation

HRID 1052394 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:12]1[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16](=[O:24])[C:15]2=[C:25](Br)[CH:26]=[CH:27][N:14]2[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:37]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:12]1[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16](=[O:24])[C:15]2=[C:25]([CH3:37])[CH:26]=[CH:27][N:14]2[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 131736130(S)-tert-Butyl (3-(benzyloxy)-1-(5-bromo-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamate

Product 1

HCID 131736131(S)-tert-Butyl (3-(benzyloxy)-1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamateYield 85.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

(S)-tert-Butyl (3-(benzyloxy)-1-(5-bromo-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamate (0.6 g, 1.08 mmol) was dissolved in 36 mL anhydrous dimethylformamide in a pressure reactor vessel. 2,4,6-Trimethylboroxine (1.36 mL, 9.76 mmol), potassium carbonate (3 g, 21.68 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.13 g, 0.11 mmol) were added under argon conditions. The reaction mixture was heated at 120° C. for 2 h and then cooled and filtered through a plug of Celite, washing several times with ethyl acetate. The combinated filtrates were washed with water, saturated ammonium chloride solution and brine, dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified using SP1® Purification System (0% to 20%, hexane-ethyl acetate) to give 0.45 g (85% yield) of the title compound as a white solid.

Workup

  1. temperaturecooled
  2. filtrationfiltered through a plug of Celite
  3. washwashing several times with ethyl acetate
  4. washThe combinated filtrates were washed with water, saturated ammonium chloride solution and brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified
  9. customSP1® Purification System (0% to 20%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-07792c823de14ac894c2b72686c8df1a
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

Loading…