Pyridine → HCID 58266360, compound

HRID 1888475Notes

Reaction equation

HRID 1888475 reaction equation
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].[CH2:16]([N:18]1[CH2:27][CH2:26][C:25]2[C:20](=[C:21]([O:29][CH3:30])[CH:22]=[C:23](O)[CH:24]=2)[CH2:19]1)[CH3:17].N1C=CC=CC=1>C(Cl)Cl>[CH2:16]([N:18]1[CH2:27][CH2:26][C:25]2[C:20](=[C:21]([O:29][CH3:30])[CH:22]=[C:23]([O:8][S:1]([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2])[CH:24]=2)[CH2:19]1)[CH3:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 58266415HCID 58266415, compound

Product 1

HCID 58266360HCID 58266360, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triflic anhydride (0.54 mL, 3.2 mmol) was added dropwise over 15 minutes to a suspension of 2-ethyl-8-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol (328 mg, 1.6 mmol) in pyridine (0.52 mL, 6.4 mmol) and DCM (15 mL). The reaction mixture was allowed to warm to ambient temperature and stirred for 2 h. The mixture was diluted with DCM (60 mL), washed with water (100 mL), dried over sodium sulfate, filtered and evaporated in vacuo. The resultant solid was purified by flash chromatography (silica, 12 g column, ISCO, 0-100% ethyl acetate in pentane) to afford the title compound as a yellow solid (341 mg, 63%). 1H NMR (CDCl3, 300 MHz): 6.76 (d, J=2.3 Hz, 1H), 6.68 (d, J=2.3 Hz, 1H), 4.30-4.10 (m, 2H), 3.87 (s, 3H), 3.50-3.37 (m, 2H), 3.36-3.10 (s, 4H), 1.51 (t, J=7.2 Hz, 3H). LCMS (Method B): RT=2.39 min, M+H+=340.

Workup

  1. washwashed with water (100 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe resultant solid was purified by flash chromatography (silica, 12 g column, ISCO, 0-100% ethyl acetate in pentane)

Sources & evidence

ORD record
ord-9f62b81bd6314e48b962e4470b0fb5a9
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

Loading…