Stannane, tributyl(1-ethoxyethenyl)- → HCID 59655702, compound

HRID 2054425Notes

Reaction equation

HRID 2054425 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:6]2[N:5]=[C:4]([CH3:25])[N:3]=1.C([Sn](CCCC)(CCCC)[C:31]([O:33][CH2:34][CH3:35])=[CH2:32])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>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:9]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[C:6]2[N:5]=[C:4]([CH3:25])[N:3]=[C:2]([C:31]([O:33][CH2:34][CH3:35])=[CH2:32])[N:7]2[N:8]=1

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 59655729HCID 59655729, compound

Product 1

HCID 59655702HCID 59655702, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

To a mixture of 4-chloro-7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methylpyrazolo[1,5-a][1,3,5]triazine (I-2A-1b; 100 mg, 0.257 mmol) and tetrakis(triphenylphosphine)palladium(0) (15 mg, 0.013 mmol) in DMF (0.8 ml) was added tributyl(1-ethoxyvinyl)tin (130 mg, 0.36 mmol) in DMF (1.5 ml). The reaction was degassed (3×) by pulling a vacuum and refilling with nitrogen. After heating at 100° C. for 1 hour under nitrogen, the reaction was cooled and then extracted from water with ethyl acetate. The organic layer was washed with ½ saturated brine and then brine. After drying (MgSO4), the mixture was concentrated, in vacuo, and purified on a Biotage™ Flash 12M column using 10% ethyl acetate in hexanes to afford product 14A-1 as a solid (53 mg, 49%): +APcI MS (M+1) 425.1; 1H NMR (400 MHz, CD3OD) δ 7.50-7.38 (m, 6H), 7.27 (d, J=8.7 Hz, 2H), 6.20 (d, J=3.3 Hz, 1H), 5.19 (d, J=3.3 Hz, 1H), 4.05 (q, J=7.1 Hz, 2H), 2.75 (s, 3H), 1.45 (t, J=7.1 Hz, 3H).

Workup

  1. customThe reaction was degassed (3×)
  2. temperaturethe reaction was cooled
  3. extractionextracted from water with ethyl acetate
  4. washThe organic layer was washed with ½ saturated brine
  5. dry with materialAfter drying (MgSO4)
  6. concentrationthe mixture was concentrated, in vacuo
  7. custompurified on a Biotage™ Flash 12M column

Sources & evidence

ORD record
ord-0091d845a3584328aea94cc10093dde6
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

Loading…