2-(Di-tert-butylphosphino)biphenyl → 2-{4-[4-(4-Ethoxy-phenyl)-piperidin-1-yl]-phenyl}-N-ethyl-propionamide

HRID 409740Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)[CH3:2].Br[C:17]1[CH:22]=[CH:21][C:20]([CH:23]([CH3:29])[C:24]([NH:26][CH2:27][CH3:28])=[O:25])=[CH:19][CH:18]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>O1CCOCC1>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:11][CH2:12][N:13]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]([CH3:29])[C:24]([NH:26][CH2:27][CH3:28])=[O:25])=[CH:19][CH:18]=3)[CH2:14][CH2:15]2)=[CH:6][CH:5]=1)[CH3:2]

Participants

Conditions

Temperature: 45 °C

Procedure

41 mg (0.20 mmol) 4-(4-Ethoxy-phenyl)-piperidine (XV.1) are added to a mixture of 51 mg (0.20 mmol) 2-(4-bromo-phenyl)-N-ethyl-propionamide (IV.3), 77 mg (0.80 mmol) sodium tert-butyrat, 24 mg (0.08 mmol) 2-(di-tert-butylphosphino)biphenyl and 18 mg (0.02 mmol) tris-(dibenzylidenaceton)-dipalladium(0) in 1 mL 1,4-dioxane. The mixture is stirred for 12 h at 45° C. After that time, the solvent is removed in vacuo and the residue is purified by HPLC (column: Waters XBridge 50; eluent A: water+0.1% NH4OH, eluent B: MeOH) to yield the desired product.

Workup

customAfter that time, the solvent is removed in vacuo
customthe residue is purified by HPLC (column: Waters XBridge 50; eluent A: water+0.1% NH4OH, eluent B: MeOH)

Sources & evidence

ORD record: ord-778e217f796449c9953eac831c2ec7ef
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759528B2

Reaction notes

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