2,6-Lutidine → HCID 10500406, compound

HRID 411300Notes

Reaction equation

HRID 411300 reaction equation
[CH3:1][O:2][C:3]1[C:16]2[C:7](=[N:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]([O:17][CH3:18])=[CH:5][CH:4]=1.N1C(C)=CC=CC=1C.[F:27][C:28]([F:41])([F:40])[S:29]([O:32]S(C(F)(F)F)(=O)=O)(=[O:31])=[O:30]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]1[C:16]2[C:7](=[N:8][C:9]3[C:14]([C:15]=2[O:32][S:29]([C:28]([F:41])([F:40])[F:27])(=[O:31])=[O:30])=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]([O:17][CH3:18])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 18540874HCID 18540874, compound

Product 1

HCID 10500406HCID 10500406, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1,4-dimethoxyacridine (prepared as described in Ionescu and Mester (1969)) (1.0 g, 3.9 mmol) in dry CH2Cl2 (18 ml) under N2 were successively added DMAP (95 mg, 0.8 mmol), 2,6-lutidine (0.6 ml, 55 mmol) and trifluoromethane-sulfonic anhydride (0.8 ml, 4.7 mmol) and the reaction mixture was stirred at 0° C. for 2 h and then for 1 h at rt. The solution was washed with H2O, dried and evaporated. The residue was purified by column chromatography when elution with hexane/CH2Cl2 (1:1) to give the title compound (1.3 g, 87%), as a yellow solid. IR (KBr): ν/cm−1=1253 (s, SO), 1030 (s, SO); 1H NMR (200 MHz, CDCl3): δH/ppm=4.04 (s, 3H, OCH3), 4.14 (s, 3H, OCH3), 6.83 (d, J=8.4 Hz, 1H, H-2), 7.01 (d, J=8.4 Hz, 1H, H-3), 7.68 (dd, J=8.5 and 7.8 Hz, 1H, H-7), 7.86 (dd, J=8.5 and 7.8 Hz, 1H, H-6), 8.22 (d, J=8.5 Hz, 1H, H-5), 8.43 (d, J=8.5 Hz, 1H, H-8); 13C NMR (50.3 MHz, CDCl3): δC/ppm=55.2 (q, OCH3) 56.3 (q, OCH3), 104.2 (d, C-2), 106.6 (d, C-3), 113.3 (s, C-9a), 118.5 (q, CF3), 119.1 (s, C-8a), 120.7 (d, C-7), 122.5 (s, C-4a), 127.6 (d, C-6), 129.8 (d, C-8), 130.9 (d, C-5), 144.2 (s, C-10a), 147.2 (s, C-1), 148.7 (s, C-4), 148.8 (s, C-9); MS (EI); m/z (%)=388 [M+1] (9), 387 [M+] (42), 254 (100), 226 (69); HRMS: calcd. for C16H12F3NO5S 387.0388; found 387.0394.

Workup

  1. waitfor 1 h at rt
  2. washThe solution was washed with H2O
  3. customdried
  4. customevaporated
  5. customThe residue was purified by column chromatography when elution with hexane/CH2Cl2 (1:1)

Sources & evidence

ORD record
ord-2d70d9bcbff24c8a9376463865db9af4
Source dataset
uspto-grants-2003_05
Patent number
US06559161B1

Reaction notes

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