2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 16665186, compound

HRID 1927619Notes

Reaction equation

HRID 1927619 reaction equation
[CH2:1]([NH:3][C:4](=[O:18])[CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)[CH3:2].Br[C:20]1[CH:33]=[CH:32][C:23]([C:24]([NH:26][CH:27]([CH2:30][CH3:31])[CH2:28][CH3:29])=[O:25])=[CH:22][C:21]=1[F:34].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([NH:3][C:4]([CH:5]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH:6]1[CH2:7][CH2:8][N:9]([C:20]2[CH:33]=[CH:32][C:23]([C:24]([NH:26][CH:27]([CH2:28][CH3:29])[CH2:30][CH3:31])=[O:25])=[CH:22][C:21]=2[F:34])[CH2:10][CH2:11]1)=[O:18])[CH3:2]

Participants

7

Reactant 4

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 48474221HCID 48474221, compoundHCID 69304327HCID 69304327, compound

Product 1

HCID 16665186HCID 16665186, compoundYield 1.5%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-ethyl-2-phenyl-2-piperidin-4-yl-acetamide (90 mg, 0.3 mmol), 4-bromo-N-(1-ethyl-propyl)-3-fluoro-benzamide (prepared as in Example 113, Step A; 120 mg, 0.4 mmol), Pd2(dba)3 (6 mg, 0.007 mmol), X-Phos (3 mg, 0.006 mmol), and NaOtBu (70 mg, 0.7 mmol) in toluene (3 mL) was heated at 100° C. for 18 h. The solids were removed by filtration and the filtrate was concentrated to give an oil, which was purified by PTLC to give a white solid (2 mg, 1%). MS (ESI): mass calcd. for C27H36FN3O2, 453.59; m/z found, 454.5 [M+H]+. 1H NMR (CDCl3): 7.69-7.67 (m, 2H), 7.60-7.58 (m, 2H), 7.44-7.43 (m, 1H), 7.41 (s, 1H), 7.36-7.31 (m, 4H), 6.89 (t, J=8.5, 1H), 5.64-5.62 (m, 1H), 5.48-5.45 (m, 1H), 3.99-3.96 (m, 1H), 3.74-3.70 (m, 1H), 3.56-3.53 (m, 1H), 3.44-3.41 (m, 1H), 3.36-3.30 (m, 1H), 3.21-3.15 (m, 1H), 2.91-2.88 (m, 1H), 2.80-2.75 (m, 1H), 2.64-2.58 (m, 1H), 2.29-2.26 (m, 1H), 2.04-2.00 (m, 1H), 1.65-1.61 (m, 1H), 1.49-1.43 (m, 1H), 1.27-1.23 (m, 1H), 1.09 (t, J=7.3, 3H), 0.93 (t, J=7.4, 6H).

Workup

  1. customThe solids were removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customto give an oil, which
  4. customwas purified by PTLC

Sources & evidence

ORD record
ord-2c336083f45241b1b8a463a3b8bc9f32
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

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