Hydrochloric Acid → HCID 12968631, compound

HRID 1246971Notes

Reaction equation

HRID 1246971 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:18]=[CH:17][C:13]3[O:14][CH2:15][O:16][C:12]=3[CH:11]=2)[C:5]([C:19]#[N:20])=[C:4](SC2C=CC=CC=2)[N:3]=1.[CH:28]1([Mg]Br)[CH2:30][CH2:29]1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.C(OCC)C.O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:18]=[CH:17][C:13]3[O:14][CH2:15][O:16][C:12]=3[CH:11]=2)[C:5]([C:19]#[N:20])=[C:4]([CH:28]2[CH2:30][CH2:29]2)[N:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 11245724HCID 11245724, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 12968631HCID 12968631, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Under an atmosphere of argon, 2-amino-4-(1,3-benzodioxol-5-yl)-6-(phenyl-sulfanyl)-3,5-dicyanopyridine [preparation analogously to J. M. Quintela, J. L. Soto, Anales de Quimica 79, 368–372 (1983)] (100 mg, 0.27 mmol) is dissolved in absolute THF (3 ml). 1,3-Bis(diphenylphosphino)propanedichloronickel(II) (4.4 mg, 0.008 mmol) is added, the color of the solution changing to pink. On slow dropwise addition of cyclopropylmagnesium bromide (1M solution in THF; 0.644 ml, 0.644 mmol), a clear change in color to brown-red can be observed. The solution is heated at 50° C. for 3 hours. After only about 5 minutes, the solution turns green. 1N hydrochloric acid (1 ml) is added and the mixture is then diluted with diethyl ether. Solid sodium carbonate and water are added. The phases are separated and the organic phase is dried over magnesium sulfate, filtered and concentrated. The mixture is separated by silica gel column chromatography (toluene:ethyl acetate=2:1).

Workup

  1. addition1,3-Bis(diphenylphosphino)propanedichloronickel(II) (4.4 mg, 0.008 mmol) is added
  2. customThe phases are separated
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe mixture is separated by silica gel column chromatography (toluene:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-da00cb7f803b4ab88cd908d659fc2a03
Source dataset
uspto-grants-2006_10
Patent number
US07129255B2

Reaction notes

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