Cyclohexene → HCID 58415359, compound

HRID 2075236Notes

Reaction equation

HRID 2075236 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]2[CH:17]=[C:16]([C:18]3[CH:32]=[CH:31][C:21]([CH2:22][N:23]4[CH2:26][CH:25]([C:27]([O:29][CH3:30])=[O:28])[CH2:24]4)=[CH:20][C:19]=3[F:33])[O:15][C:11]2=[C:12](Cl)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCCCC=1>CCO.[Pd]>[CH2:1]([C:8]1[CH:9]=[C:10]2[CH:17]=[C:16]([C:18]3[CH:32]=[CH:31][C:21]([CH2:22][N:23]4[CH2:24][CH:25]([C:27]([O:29][CH3:30])=[O:28])[CH2:26]4)=[CH:20][C:19]=3[F:33])[O:15][C:11]2=[CH:12][N:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 58415409HCID 58415409, compound

Product 1

HCID 58415359HCID 58415359, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of methyl 1-(4-(5-benzyl-7-chlorofuro[2,3-c]pyridin-2-yl)-3-fluorobenzyl)azetidine-3-carboxylate (0.320 g, 0.69 mmol), cyclohexene (1.00 mL, 9.9 mmol), palladium (10 wt. % on activated carbon, 0.320 g, 3.0 mmol) in EtOH (6.0 mL) was prepared in a sealed tube and heated under N2 to 85° C. for 4 h. The mixture was filtered through Celite, and the filtrate evaporated purified by flash chromatography using EtOAc/hexanes to give title compound. 1H NMR (300 MHz, CDCl3) δ ppm 8.82 (s, 1H), 7.96 (t, J=7.7 Hz, 1H), 6.99-7.38 (m, 9H), 4.25 (s, 2H), 3.72 (s, 3H), 3.65 (s, 2H), 3.48-3.59 (m, 2H), 3.33-3.39 (m, 3H). MS (ESI) m/z: Calculated; 430.2 Observed: 431.2 (M++1).

Workup

  1. customwas prepared in a sealed tube
  2. filtrationThe mixture was filtered through Celite
  3. customthe filtrate evaporated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-a0c038241a0344dda19f62e61f60226f
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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