Ethyl Acetate → HCID 58190565, compound

HRID 1959754Notes

Reaction equation

HRID 1959754 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][N:13]1[C:17]3=[N:18][C:19](Br)=[CH:20][N:21]=[C:16]3[N:15]=[N:14]1)=[CH:7][CH:6]=2.C([Sn](CCCC)(CCCC)C([O:30][CH2:31][CH3:32])=C)CCC.[CH3:41][CH2:42][O:43]C(C)=O>CN(C=O)C.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>[C:42]([C:19]1[N:18]=[C:17]2[N:13]([CH2:12][C:8]3[CH:9]=[C:10]4[C:5](=[CH:6][CH:7]=3)[N:4]=[CH:3][C:2]([C:31](=[O:30])[CH3:32])=[CH:11]4)[N:14]=[N:15][C:16]2=[N:21][CH:20]=1)(=[O:43])[CH3:41]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 58190582HCID 58190582, compound

Product 1

HCID 58190565HCID 58190565, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-bromo-6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (128 mg, 0.305 mmol), Pd(PPh3)4 (51.5 mg, 0.045 mmol) and tributyl(1-ethoxyvinyl)stannane (253 mg, 0.701 mmol) in 5 mL of DMF was heated at 95° C. for 1 h under nitrogen. The reaction mixture was diluted with EtOAc, washed with water. The organic layer was separated, dried over Na2SO4, filtered and concentrated in vacuo. The residue was dissolved in HOAc and 3 N HCl, and stirred at rt for 3 h. The solvent was removed under reduced pressure and the residue was dissolved in DCM, washed with saturated aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with DCM/MeOH gradient to afford the title compound (74 mg, 45%) as a yellow solid. 1H-NMR (400 MHz, CDCl3) δ ppm 9.47-9.45 (m, 2H), 8.70 (d, 1H), 8.19 (d, 1H), 8.05 (d, 1H), 7.97 (dd, 1H), 6.21 (s, 2H), 2.82 (s, 3H), 2.74 (s, 3H). LCMS (method E): [MH]+=347, tR=4.503 min.

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in HOAc
  7. customThe solvent was removed under reduced pressure
  8. dissolutionthe residue was dissolved in DCM
  9. washwashed with saturated aqueous NaHCO3 and brine
  10. dry with materialThe organic layer was dried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe residue was purified by flash chromatography on silica gel eluting with DCM/MeOH gradient

Sources & evidence

ORD record
ord-8e12a435c0e541c8a3b36ad7f7a6541b
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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