Ethyl Acetate → HCID 59341976, compound

HRID 456135Notes

Reaction equation

HRID 456135 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[N:9]=[N:10][C:5]2=[N:4][CH:3]=1.[C:22]([Zn]C#N)#[N:23].[NH4+].[Cl-].CCOC(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>[N:18]1[C:19]2[C:14](=[CH:13][C:12]([CH2:11][N:8]3[C:6]4=[N:7][C:2]([C:22]#[N:23])=[CH:3][N:4]=[C:5]4[N:10]=[N:9]3)=[CH:21][CH:20]=2)[CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 547756086-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinolineHCID 178514179HCID 178514179, compound

Product 1

HCID 59341976HCID 59341976, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
127 °C

Procedure

To a degassed solution of 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (1.6 g, 4.69 mmol) in DMF (8 mL), was added Pd(PPh3)4 (0.434 g, 0.375 mmol) and dicyanozinc (0.441 g, 3.75 mmol). The reaction mixture was heated to 127° C. for 4 h. NH4Cl(aq) was added to quench the reaction, followed by EtOAc. The reaction mixture was filtered through celite, washed with saturated NaHCO3 and NH4Cl. The organic layer was separated, dried over Na2SO4, filtered and concentrated to give a crude product, which was purified with Analogix gel silica (Hexanes:EtOAc) to afford the title compound as a light yellow solid. LCMS (method B): [MH]+=288, tR=1.81 min.

Workup

  1. customto quench
  2. customthe reaction
  3. filtrationThe reaction mixture was filtered through celite
  4. washwashed with saturated NaHCO3 and NH4Cl
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a crude product, which
  10. customwas purified with Analogix gel silica (Hexanes:EtOAc)

Sources & evidence

ORD record
ord-de8c61cde6b44b488eb9b934e2451ecb
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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