Pyridine → HCID 58266360, compound

HRID 1505937Notes

Reaction equation

HRID 1505937 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-b8869ba8b6fa4cc3be3e39c143a04c67
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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