Triphenylarsine → HCID 10192938, compound

HRID 1179131Notes

Reaction equation

HRID 1179131 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[CH:9][C:10]2[N:11]([N:13]=[CH:14][C:15]=2[C:16]2[CH:21]=[CH:20][N:19]=[C:18]([NH:22][CH:23]3[CH2:25][CH2:24]3)[N:17]=2)[N:12]=1)(=O)=O.[Li+].[Cl-].[CH:30]1C=CC([As](C2C=CC=CC=2)C2C=CC=CC=2)=C[CH:35]=1.C([Sn](CCCC)(CCCC)CCCC)=C>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH:23]1([NH:22][C:18]2[N:17]=[C:16]([C:15]3[CH:14]=[N:13][N:11]4[C:10]=3[CH:9]=[CH:8][C:7]([CH:30]=[CH2:35])=[N:12]4)[CH:21]=[CH:20][N:19]=2)[CH2:25][CH2:24]1

Participants

8

Reactant 4

HCID 11773TriphenylarsineHCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 10172978HCID 10172978, compound

Product 1

HCID 10192938HCID 10192938, compoundYield 93.4%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-[2-(cyclopropylamino)-4-pyrimidinyl]pyrazolo[1,5-b]pyridazin-6-yl trifluoromethanesulfonate (100 mg, 0.25 mmol) in DMF (3 mL) was added Pd2(dba)3 (12 mg, 0.0125 mmol), LiCl (32 mg, 0.75 mmol), AsPh3 (31 mg, 0.10 mmol), and vinyl-tributylstannane (120 mg, 0.375 mmol). The reaction mixture was heated at an oil bath temperature of 60° C. for about 4 hours. The mixture was cooled to RT and water (20 mL) was added. The aqueous layer was washed with EtOAc (3×50 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo and purified by silica-gel column chromatography (gradient, 10-80% EtOAc in hexanes) to give the title compound as an off-white solid (26 mg, 37%). 1H-NMR (300 MHz, CDCl3). δ 9.05 (d, 1H, J=9.3 Hz), 8.44 (s, 1H), 8.30 (d, 1H, J=5.3 Hz), 7.40 (d, 1H, J=9.4 Hz), 6.92 (m, 2H), 6.22 (d, 1H, J=17.7 Hz), 5.75 (d, 1H, J=11.2 Hz), 5.48 (bs, 1H), 2.86 (m, 1H), 0.90 (m, 2H), 0.66 (m, 2H); MS (ESI) (M+H)+ 279.

Workup

  1. temperatureThe mixture was cooled to RT
  2. washThe aqueous layer was washed with EtOAc (3×50 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by silica-gel column chromatography (gradient, 10-80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-62603e33b7244d3ba2377dbeee9a138b
Source dataset
uspto-grants-2007_10
Patent number
US07279473B2

Reaction notes

Loading…