Ethanol → HCID 11162122, compound

HRID 1824726Notes

Reaction equation

HRID 1824726 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].C(C1C=CC=C(C(C)C)C=1[N+]1C=[CH:26][N:25]([C:28]2[C:33]([CH:34]([CH3:36])[CH3:35])=[CH:32][CH:31]=[CH:30][C:29]=2[CH:37]([CH3:39])C)[CH:24]=1)(C)C.[C:40]([O-:43])([O-])=O.[Na+].[Na+].C(O)C>C(Cl)Cl.CO.N.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]>[C:1]1([C:29]2[CH:37]=[CH:39][C:40]3[O:43][C:33]4([CH2:28][N:25]5[CH2:24][CH2:35][CH:34]4[CH2:36][CH2:26]5)[CH2:32][C:31]=3[CH:30]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 27349131,3-Bis(2,6-diisopropylphenyl)imidazolium chloride

Product 1

HCID 11162122HCID 11162122, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 12896473Azane;hydrateSolvent

Procedure

Under N2, the mixture of the product of 1E (200 mg, 0.68 mmol), phenylboronic acid (Aldrich, 276 mg, 1.36 mmol), Pd2(dba)3 (Strem Chemicals, 12.4 mg, 0.014 mmol) and 1,3-bis(2,6-di-i-propylphenyl)imidazolium chloride, (Strem Chemicals, 95%, 18.3 mg, 0.041 mmol) in Na2CO3 (aqueous, 2M, 2 mL, 4 mmol) and ethanol (8 mL) was stirred at 80° C. for 15 hours. The reaction was monitored with TLC. After the reaction was complete, it was concentrated under reduced pressure and the residue was diluted with EtOAc (30 mL). It was then washed with brine (2×5 mL). The organic solution was concentrated and the title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:2, Rf. 0.40) as oil (90 mg, 45% yield). 1H NMR (MeOH-d4, 300 MHz) δ 1.52–1.62 (m, 1H), 1.68–1.89 (m, 2H), 2.00–2.06 (m, 1H), 2.14–2.25 (m, 1 H), 2.81–3.32 (m, 7H), 3.47 (d, J=15.9 Hz, 1H), 6.76 (d, J=8.6 Hz, 1H), 7.24 (tt, J=7.1, 1.2 Hz, 1H), 7.32–7.42 (m, 4H), 7.49–53 (m, 1H) ppm. MS (DCl/NH3) m/z 292 (M+H)30 .

Workup

  1. concentrationit was concentrated under reduced pressure
  2. additionthe residue was diluted with EtOAc (30 mL)
  3. washIt was then washed with brine (2×5 mL)
  4. concentrationThe organic solution was concentrated

Sources & evidence

ORD record
ord-758abe5b2c4e4d168ed040808c973779
Source dataset
uspto-grants-2006_05
Patent number
US07045530B2

Reaction notes

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