Stannane, tributyl(1-ethoxyethenyl)- → 6-[6-(1-Ethoxy-vinyl)[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl]-quinoline

HRID 456123

Reaction equation

HRID 456123 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([Sn](CCCC)(CCCC)[C:27]([O:29][CH2:30][CH3:31])=[CH2:28])CCC>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>[CH2:30]([O:29][C:27]([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)=[CH2:28])[CH3:31]

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 547756086-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

Product 1

HCID 248519576-[6-(1-Ethoxy-vinyl)[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl]-quinolineYield 62%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a degassed solution of 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quino-line (2.50 g, 5.86 mmol) in DMF (20 mL), was added Pd(Ph3P)4 (0.542 g, 0.469 mmol) and the solution was stirred for 20 min at room temperature. Then tributyl(1-ethoxyvinyl)stannane (2.117 g, 5.86 mmol) was added. The reaction was heated to 100° C. until LC-MS showed the reaction was complete. The reaction mixture was filtered through celite and the filtrate was washed with water, dried over Na2SO4, and concentrated. The resulting crude product was purified by silica gel column chromatography with gradient Hex:EA to give 6-((6-(1-ethoxyvinyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (1.2 g, 62%). 1H-NMR (400 MHz, CDCl3) δ ppm 9.19 (s, 1H), 8.94 (m, 1H), 8.20 (m, 1H), 7.99 (s, 1H), 7.89 (d, 1H), 7.548 (m, 1H), 6.12 (s, 2H), 5.61 (d, 1H), 4.61 (d, 1H), 4.05 (q, 2H), 1.51 (t, 3H). LCMS (method B): [MH]+=360, tR=2.40 min.

Workup

  1. temperatureThe reaction was heated to 100° C. until LC-MS
  2. filtrationThe reaction mixture was filtered through celite
  3. washthe filtrate was washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe resulting crude product was purified by silica gel column chromatography with gradient Hex

Sources & evidence

ORD record
ord-9ddbe9a47e2f462aa04988cf1af11304
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Linked notes

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