Pyridine → HCID 86623627, compound

HRID 1821028Notes

Reaction equation

HRID 1821028 reaction equation
N1C=CC=CC=1.[F:7][C:8]([F:21])([F:20])[S:9]([O:12]S(C(F)(F)F)(=O)=O)(=[O:11])=[O:10].O[C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][C:31]=1[CH3:32])[CH:28]([CH2:33][C:34]([O:36][CH3:37])=[O:35])[CH2:27][CH2:26]2>ClCCl>[F:7][C:8]([F:21])([F:20])[S:9]([O:12][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][C:31]=1[CH3:32])[CH:28]([CH2:33][C:34]([O:36][CH3:37])=[O:35])[CH2:27][CH2:26]2)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 86057442HCID 86057442, compound

Product 1

HCID 86623627HCID 86623627, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of pyridine (0.13 mL, 1.61 mmol) in dichloromethane (1.0 mL) cooled to 0° C. trifluoromethanesulfonic anhydride (0.25 mL, 1.47 mmol) was added. The resultant mixture was stirred for 5 min and methyl (5-hydroxy-6-methylindan-1-yl)acetate (295 mg, 1.34 mmol, from Step D) was added as a solid. The reaction mixture was warmed to ambient temperature, stirred for 30 min and diluted with dichloromethane. The organic layer was washed with H2O, brine and dried over MgSO4. The mixture was filtered and concentrated in vacuo. Purification by flash chromatography (10% EtOAc/hexanes) on SiO2 gave 405 mg of the title compound as a pale yellow liquid: 1H NMR (500 MHz, CDCl3) δ 1.69-1.91 (m, 1H), 2.33 (s, 3H), 2.38-2.56 (m, 2H), 2.69-2.79 (m, 1H), 2.79-3.01 (m, 2H), 3.49-3.65 (m, 1H), 3.76 (s, 3H), 7.09 (s, 2H).

Workup

  1. additionwas added
  2. washThe organic layer was washed with H2O, brine
  3. dry with materialdried over MgSO4
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (10% EtOAc/hexanes) on SiO2

Sources & evidence

ORD record
ord-9719a97887ea4d7fb4f60190fdfecc85
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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