Isopropanol → HCID 69231962, compound

HRID 73294Notes

Reaction equation

HRID 73294 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].[C:12]([O-:15])([O-])=O.[Cs+].[Cs+].[CH:18](O)([CH3:20])[CH3:19]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:15][CH2:12][CH2:19][C@@H:18]1[CH2:20][C@H:1]1[C:3]1[CH:8]=[CH:7][C:6]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 10796Cesium carbonateHCID 27343264-Cyanophenylboronic acid

Product 1

HCID 69231962HCID 69231962, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

A solution of Example 26F (1.2 g, 5 mmol), 4-cyanophenylboronic acid [CAS 126747-14-6] (1.46 g, 2 equivalents), Pd(PPh3)2Cl2 (350 mg), and Cs2CO3 (6.5 g) in isopropanol (80 mL) under N2 was stirred at reflux overnight. The mixture was partitioned between ethyl acetate and H2O. The organic layer was washed with saturated aqueous NaHCO3 and then with brine. The organic layer was then dried (MgSO4) and filtered. The filtrate was concentrated in vacuo and the resulting residue was purified by chromatography on silica gel eluted with 4.1 hexanes/ethyl acetate to provide the title compound. 1H NMR (300 MHz, CDCl3): δ 0.85-1.03 (m, 2H), 1.12-1.2 (m, 1H), 1.65-1.7 (m, 3H), 3.78 (t, J=6 Hz, 2H), 7.15 (d, J=9 Hz, 2H), 7.48 (d, J=9 Hz, 2H), 7.68 (q, J=9 Hz, 4H). MS (DCl—NH3) m/z 264 (M+H)+.

Workup

  1. temperatureat reflux overnight
  2. customThe mixture was partitioned between ethyl acetate and H2O
  3. washThe organic layer was washed with saturated aqueous NaHCO3
  4. dry with materialThe organic layer was then dried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe resulting residue was purified by chromatography on silica gel
  8. washeluted with 4.1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-e318dd91a7b5485db1a467c821712910
Source dataset
uspto-grants-2014_09
Patent number
US08829041B2

Reaction notes

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