Potassium Phosphate, Tribasic → HCID 89690469, compound

HRID 1481850Notes

Reaction equation

HRID 1481850 reaction equation
Cl[C:2]1[CH:19]=[C:18]([N:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])[CH2:22][CH2:21]2)[C:17]([N+:33]([O-:35])=[O:34])=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][N:10]1[CH2:14][CH2:13][CH2:12][C:11]1=[O:15])=[O:5].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:44]1(P(C2CCCCC2)C2CCCCC2)CCCC[CH2:45]1.C([Sn](CCCC)(CCCC)C=C)CCC>O1CCOCC1.O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.CO>[N+:33]([C:17]1[C:18]([N:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])[CH2:22][CH2:21]2)=[CH:19][C:2]([CH:44]=[CH2:45])=[C:3]([CH:16]=1)[C:4]([NH:6][CH2:7][CH2:8][CH2:9][N:10]1[CH2:14][CH2:13][CH2:12][C:11]1=[O:15])=[O:5])([O-:35])=[O:34]

Participants

10

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 81998TributylvinyltinHCID 89690627HCID 89690627, compound

Product 1

HCID 89690469HCID 89690469, compoundYield 100%

Reagents, catalysts & solvents 5

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolventHCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
100 °C

Procedure

2-Chloro-5-nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-4-(4-o-tolyl-piperazin-1-yl)-benzamide 1f (400.0 mg, 0.80 mmol, 100 mol %), 1M aqueous potassium phosphate, tribasic (1.6 ml, 1.60 mmol, 200 mol %), tricyclohexylphosphine (22.4 mg, 0.08 mmol, 10 mol %), tributyl-vinyl-stannane (304.4 mg, 0.96 mmol, 120 mol %) and palladium(II) acetate (9.0 mg, 0.04 mmol, 5 mol %) were dissolved in 12.0 mL of dioxane in a 40 mL scintillation vial and the vessel was sealed and heated to 100° C. for 16 h. The reaction was then diluted with water and ethyl acetate and filtered through a pad of Celite. The filtrate was extracted twice with ethyl acetate and the combined organics were dried over sodium sulfate and concentrated. After two column chromatography runs, first with dichloromethane/methanol and then with ethyl acetate/methanol, 5-nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-4-(4-o-tolyl-piperazin-1-yl)-2-vinyl-benzamide 6a (41.0 mg, 0.08 mmol, 10.4%) was obtained in pure form. LCMS (ESI) 492 (M+H).

Workup

  1. customthe vessel was sealed
  2. filtrationfiltered through a pad of Celite
  3. extractionThe filtrate was extracted twice with ethyl acetate
  4. dry with materialthe combined organics were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f912427e78f3460ab40d1fa27b6d7fc0
Source dataset
uspto-grants-2016_08
Patent number
US09409897B2

Reaction notes

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