2-Dimethylaminopyridine → HCID 22676818, compound

HRID 1006254Notes

Reaction equation

HRID 1006254 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].CN(C1C=CC=CN=1)C.[CH:25]1([CH2:28][O:29][C:30]2[CH:31]=[C:32]([C:36]3[C:44]4[C:39](=[CH:40][CH:41]=[C:42](O)[CH:43]=4)[N:38]([CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[C:49]([O:53][CH3:54])[CH:48]=4)[C:37]=3[C:55]([O:57][CH2:58][CH3:59])=[O:56])[CH:33]=[CH:34][CH:35]=2)[CH2:27][CH2:26]1>ClCCl.N1C=CC=CC=1.C(OCC)(=O)C>[CH:25]1([CH2:28][O:29][C:30]2[CH:31]=[C:32]([C:36]3[C:44]4[C:39](=[CH:40][CH:41]=[C:42]([O:8][S:1]([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2])[CH:43]=4)[N:38]([CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[C:49]([O:53][CH3:54])[CH:48]=4)[C:37]=3[C:55]([O:57][CH2:58][CH3:59])=[O:56])[CH:33]=[CH:34][CH:35]=2)[CH2:27][CH2:26]1

Participants

7

Reactant 3

HCID 218852-DimethylaminopyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 22676786HCID 22676786, compound

Product 1

HCID 22676818HCID 22676818, compoundYield 89.1%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Triflic anhydride (0.84 mL, 1.4 g, 5.0 mmol) and dimethylaminopyridine (25 mg, 0.20 mmol) were added to a cooled (0° C.) and stirred solution of ethyl 3-[3-(cyclopropylmethoxy)phenyl]-5-hydroxy-1-(3-methoxybenzyl)-1H-indole-2-carboxylate (Example 66, 1.00 g, 2.12 mmol) in dichloromethane (10 mL) and pyridine (2 mL). The reaction was warmed to rt and then stirred an additional 2 h. The solution was diluted with ethyl acetate (100 mL), washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. Flash chromatography of the residue over silica gel using 15% ethyl acetate/hexane afforded 1.14 g (89%) of desired product. The product had: 1H NMR (300 MHz, acetone-D6) δ 7.73 (d, 1 H), 7.54 (d, 1 H), 7.35-7.42 (m, 3 H), 7.20 (dd, 1 H), 7.00-7.07 (m, 2 H), 6.68-6.83 (m, 3 H), 5.88 (s, 2 H), 4.16 (q, 2 H), 3.91 (d, 2 H), 3.72 (s, 3 H), 1.25-1.35 (m, 1 H), 10.5 (t, 3 H), 0.55-0.65 (m, 2 H), 0.32-0.42 (m, 2 H); mass spectroscopy gave M+=603.1 (exact mass calc'd for C20H28F3NO7S=603.15).

Workup

  1. temperatureThe reaction was warmed to rt
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fec41ef7bdde4c0a8fd199ffc305328b
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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