Cyclohexene → HCID 86717608, compound

HRID 530270Notes

Reaction equation

HRID 530270 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:14](=[O:16])[CH3:15])=[C:11]([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.[CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=1.C(N(CC)CC)C>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:17]1([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[S:9][C:10]([C:14](=[O:16])[CH3:15])=[C:11]([CH3:13])[N:12]=3)=[CH:4][CH:3]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=1

Participants

6

Reactant 3

HCID 8079CyclohexeneHCID 8471TriethylamineHCID 86717609HCID 86717609, compound

Product 1

HCID 86717608HCID 86717608, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-iodophenylthiazole 4i (100 mg, 0.3 mmol) in dry DMF (5 mL) was charged with Pd(OAc)2 (5 mg), cyclohexene (1 mL) and triethylamine (0.5 mL). The reaction mixture was heated at 80° C. for 5 h. The reaction mixture was quenched with distilled water (10 mL) and extracted with ethyl acetate (30 mL). The organic layer was separated and dried over anhydrous Na2SO4. After evaporation of solvent under reduced pressure, the oily residue was collected and purified by silica gel flash chromatography, using hexane-ethyl acetate (9:1), to yield faint yellowish oil (35 mg, 39%). 1H NMR (CDCl3) δ 7.90 (d, J=8.1 Hz, 2 H), 7.29 (d, J=8.1 Hz, 2 H), 5.76 (m, 2 H), 2.80 (m, 1 H), 2.77 (s, 3 H), 2.55 (s, 3 H), 2.27-1.24 (m, 6 H); 13C NMR (CDCl3) δ 190.45, 169.54, 159.46, 150.94, 130.84, 130.63, 128.42, 127.60, 126.97, 126.33, 40.06, 32.98, 30.73, 29.40, 25.59, 18.45; CIMS m/z (rel intensity) 298 (MH+, 100); HRMS (EI), m/z 297.1189 M+, calcd for C18H19NOS 297.1187.

Workup

  1. customThe reaction mixture was quenched with distilled water (10 mL)
  2. extractionextracted with ethyl acetate (30 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. customAfter evaporation of solvent under reduced pressure
  6. customthe oily residue was collected
  7. custompurified by silica gel flash chromatography

Sources & evidence

ORD record
ord-507ae36c7687433c98c9ba5ab5de69a1
Source dataset
uspto-grants-2016_05
Patent number
US09353072B2

Reaction notes

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