2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl → HCID 89498037, compound

HRID 1430249Notes

Reaction equation

HRID 1430249 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:26]([C:36]3[CH:41]=[CH:40][CH:39]=[C:38](Cl)[C:37]=3[CH3:43])=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12].C1(P(C2CCCCC2)[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=2[C:57]2C(OC(C)C)=CC=CC=2OC(C)C)CCCCC1>O1CCCC1.CN1CCCC1=O.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]>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:26]([C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([CH2:57][CH:52]4[CH2:53][CH2:54][CH2:55][CH2:56][CH2:51]4)[C:37]=3[CH3:43])=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12]

Participants

6

Reactant 2

HCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenylHCID 89498113HCID 89498113, compound

Product 1

HCID 89498037HCID 89498037, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of EXAMPLE 107A (60 mg), dicyclohexyl(2′,6′-diisopropoxybiphenyl-2-yl)phosphine (RuPhos, 4.58 mg) and tris(dibenzylideneacetone)dipalladium(0) (2.25 mg) in tetrahydrofuran (0.5 mL) and 1-methyl-2-pyrrolidinone (0.5 mL) was stirred at room temperature for 5 minutes while bubbling N2 through the reaction mixture. To this solution was added 0.5 M (cyclohexylmethyl)zinc(II) bromide (0.393 mL) at room temperature. The reaction mixture in a sealed tube was heated in a preheated oil bath at 100° C. overnight and cooled. The reaction mixture was quenched with water and diluted with dichloromethane. The dichloromethane layer was washed with water and concentrated. The residue was purified by flash chromatography, and eluted with 5% ethyl acetate in dichloromethane to provide the title compound.

Workup

  1. customwhile bubbling N2 through the reaction mixture
  2. additionTo this solution was added 0.5 M (cyclohexylmethyl)zinc(II) bromide (0.393 mL) at room temperature
  3. temperaturecooled
  4. customThe reaction mixture was quenched with water
  5. additiondiluted with dichloromethane
  6. washThe dichloromethane layer was washed with water
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography
  9. washeluted with 5% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-7d48417cd7204e37acee401f9e94f97d
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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