5-Bromo-2-(trimethylsilyl)pyridine → HCID 178501134, compound

HRID 2283490Notes

Reaction equation

HRID 2283490 reaction equation
Cl[C:2]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH2:5]1)=[O:3].[Br:14][C:15]1[CH:16]=[CH:17][C:18]([Si](C)(C)C)=[N:19][CH:20]=1>CCCCCC>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([C:2]([C@H:4]2[CH2:9][CH2:8][C@H:7]([C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH2:5]2)=[O:3])=[N:19][CH:20]=1

Participants

4

Reactant 2

HCID 114816175-Bromo-2-(trimethylsilyl)pyridineHCID 178501148HCID 178501148, compound

Product 1

HCID 178501134HCID 178501134, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
110 °C

Procedure

To a flask containing methyl trans-4-(chlorocarbonyl)cyclohexanecarboxylate (8.19 g, 40 mmol) was added 5-bromo-2-(trimethylsilyl)pyridine (8.4 g, 36.4 mmol). The resulting mixture was heated to 110° C. for 10 hours. The reaction was allowed to cool to 70° C., and hexane (30 mL) was added dropwise. The resulting mixture was stirred for 14 hours at room temperature, filtered, and the residue was washed with hexane (20 mL). The beige solid was dried under nitrogen to afford methyl trans-4-[(5-bromopyridin-2-yl)carbonyl]cyclohexanecarboxylate. MS ESI calcd for C14H17BrNO3 [M+H]+ 326 and 328. found 326 and 328. 1H NMR (600 MHz, CDCl3) δ 8.70 (d, J=1.8 Hz, 1H), 7.94 (dd, J=8.4, 2.3 Hz, 1H), 7.88 (d, J=8.3 Hz, 1H), 3.78 (tt, J=11.9, 3.4 Hz, 1H), 3.66 (s, 3H), 2.32 (tt, J=12.2, 3.6 Hz, 1H), 2.08 (dd, J=13.8, 3.5 Hz, 2H), 1.99 (dd, J=13.9, 3.1 Hz, 2H), 1.60 (m, 2H), 1.45 (m, 2H).

Workup

  1. temperatureto cool to 70° C.
  2. filtrationfiltered
  3. washthe residue was washed with hexane (20 mL)
  4. customThe beige solid was dried under nitrogen

Sources & evidence

ORD record
ord-d4aa92f9cbcf4155ab33e7273030c744
Source dataset
uspto-grants-2015_09
Patent number
US09145391B2

Reaction notes

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