Triphenylphosphine → HCID 69486878, compound

HRID 1350376Notes

Reaction equation

HRID 1350376 reaction equation
C12BC(CCC1)CCC2.[CH2:10]([N:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][C@@H:18]1[CH:30]=[CH2:31])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.I[C:52]1[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=1.[OH-].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:10]([N:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][C@@H:18]1[CH2:30][CH2:31][C:52]1[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 707143-IodopyridineHCID 789669-Borabicyclo(3.3.1)nonaneHCID 17759473(S)-1,4-dibenzyl-2-vinylpiperazine

Product 1

HCID 69486878HCID 69486878, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

Prepared by the method in Example 128, using 9-borabicyclo[3.3.1]nonane (68.4 mL, 34.2 mmol, 0.5 M in THF), (S)-1,4-dibenzyl-2-vinyl-piperazine (2.5 g, 8.55 mmol), triphenylphosphine (718 mg, 2.74 mmol), tetrakis(triphenylphosphine) palladium(0)(395 mg, 0.34 mmol), 3-iodopyridine (2.63 g, 12.8 mmol) and 3M NaOH (7.0 mL, 21.0 mmol) to give title compound (1.28 g, 40%): mp 94–95.5° C.; mass spectrum (ion spray): m/z=372 (M+1). Analysis calculated for C25H29N3: C, 80.82; H, 7.87; N, 11.31. Found: C, 80.54; H, 7.76; N, 11.32.

Workup

  1. customPrepared by the method in Example 128

Sources & evidence

ORD record
ord-f4357f8d853f4baa91e4074ac4e8613f
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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