Methanesulfonic acid, trifluoro-, 6-chloro-2-pyridinyl ester → HCID 22218086, compound

HRID 1795379Notes

Reaction equation

HRID 1795379 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Cl[C:10]1[N:15]=[C:14](OS(C(F)(F)F)(=O)=O)[CH:13]=[CH:12][CH:11]=1>C1COCC1.CN1C(=O)CCC1.CCOCC>[CH2:1]([C:14]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[N:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 2

HCID 11357467Methanesulfonic acid, trifluoro-, 6-chloro-2-pyridinyl esterHCID 178444609HCID 178444609, compound

Product 1

HCID 22218086HCID 22218086, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of n-hexylmagnesium bromide (2M in Et2O, 3.3 mL) is added to a solution of 6-chloro-2-(trifluoromethanesulfonyloxy)pyridine (435 mg, 1.66 mmol) in THF (7 mL) and NMP (0.5 mL) at 0° C. The reaction mixture turns black and GC inspection indicates quantitative conversion of the substrate after 5 min reacion time. For work-up, the mixture is diluted with Et2O (20 mL) and quenched with brine (20 mL), the aqueous phase is repeatedly extracted with Et2O, the combined organic layers are dried over Na2SO4 and evaporated, and the residue is purified by flash chromatography (hexanes/ethyl acetate, 15/1) to afford 2,6-di(hexyl)pyridine as a colorless liquid (301 mg, 73%). 1H NMR (300 MHz, CDCl3): δ 7.47 (t, J=7.7 Hz, 1H), 6.93 (d, J=7.7 Hz, 2H), 2.70 (t, J=7.8 Hz, 4H), 1.68 (m, 4H), 1.32 (m, 12H), 0.88 (t, J=6.5 Hz, 6H). 13C NMR (75 MHz, CDCl3): δ 161.9, 136.2, 119.5, 38.5, 31.8, 30.0, 29.1, 22.7, 13.9. IR: 3060, 2955, 2926, 2871, 2856, 1590, 1577, 1456, 1378, 750 cm−1. MS m/z (rel. intensity) 247 (5, [M+]), 218 (7), 204 (22), 190 (23), 177 (100), 134 (12), 120 (44), 107 (15). HR-MS (C17H29N) calcd. 247.229999; found 247.229778.

Workup

  1. customafter 5 min
  2. customquenched with brine (20 mL)
  3. extractionthe aqueous phase is repeatedly extracted with Et2O
  4. dry with materialthe combined organic layers are dried over Na2SO4
  5. customevaporated
  6. customthe residue is purified by flash chromatography (hexanes/ethyl acetate, 15/1)

Sources & evidence

ORD record
ord-1805c4be942440c89f0103cf4b7756b0
Source dataset
uspto-grants-2006_04
Patent number
US07026478B2

Reaction notes

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