Triethylsilane → HCID 178507495, compound

HRID 538049Notes

Reaction equation

HRID 538049 reaction equation
[CH:1]1([C:4]([N:6]2[CH2:11][CH2:10][N:9]([C:12]([C@H:14]3[CH2:19][CH2:18][C@H:17]([CH2:20][NH:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[N+:29]([O-])=O)[CH2:16][CH2:15]3)=[O:13])[CH2:8][CH2:7]2)=[O:5])[CH2:3][CH2:2]1.[F-].[K+].C([SiH](CC)CC)C>CC([O-])=O.CC([O-])=O.[Pd+2]>[NH2:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[CH2:22][NH:21][CH2:20][C@H:17]1[CH2:16][CH2:15][C@H:14]([C:12]([N:9]2[CH2:10][CH2:11][N:6]([C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:5])[CH2:7][CH2:8]2)=[O:13])[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 522689Potassium FluorideHCID 178519260HCID 178519260, compound

Product 1

HCID 178507495HCID 178507495, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

(4-Cyclopropanecarbonyl-piperazin-1-yl)-{trans-4-[(2-nitrobenzylamino)-methyl]-cyclohexyl}methanone (272 mg, 0.63 mmol) and Pd(OAc)2 (7 mg, 0.03 mmol) were weighed into a flask and flushed with nitrogen for 5 minutes. THF (10 mL) was added, followed by a solution of KF (73 mg, 1.26 mmol in 1.2 ml of H2O). Then triethylsilane (0.40 mL, 2.52 mmol) was added drop wise and the reaction was left stirring for 3 h at room temperature. The mixture was filtered on a celite bed to remove palladium and the solution was concentrated under reduced pressure. The residue was suspended in DCM (4 mL) and washed with H2O (4 mL). The organic phase was collected and concentrated, the crude product was purified by SiO2 column, eluting with AcOEt:MeOH 80:20, affording 146 mg of the titled compound (57% yield).

Workup

  1. customflushed with nitrogen for 5 minutes
  2. additionTHF (10 mL) was added
  3. waitthe reaction was left
  4. filtrationThe mixture was filtered on a celite bed
  5. customto remove palladium
  6. concentrationthe solution was concentrated under reduced pressure
  7. washwashed with H2O (4 mL)
  8. customThe organic phase was collected
  9. concentrationconcentrated
  10. customthe crude product was purified by SiO2 column
  11. washeluting with AcOEt:MeOH 80:20

Sources & evidence

ORD record
ord-829b12363d24437f82a578b26facd195
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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