Trifluoroacetic acid → 6-phenyl-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2(1H)-one

HRID 710926Notes

Reaction equation

HRID 710926 reaction equation
C([O:5][C:6]1[CH:11]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH:9]=[C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:7]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:21]1([C:8]2[NH:7][C:6](=[O:5])[CH:11]=[C:10]([C:12]3[C:20]4[C:15](=[N:16][CH:17]=[CH:18][CH:19]=4)[NH:14][CH:13]=3)[CH:9]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 674423983-(2-tert-butoxy-6-phenylpyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 534948176-phenyl-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of EXAMPLE 34D in 1 mL dichloromethane was added 1 mL trifluoroacetic acid. The solution was stirred at room temperature for 25 minutes and the solvent was removed. The crude material was diluted with ethyl acetate and washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated to give the title compound. MS (ESI) m/e 287.9 (M+H)+; 1H NMR (DMSO-d6) δ 6.70 (s, 1H), 7.03 (s, 1H), 7.11-7.30 (m, 1H), 7.37-7.64 (m, 3H), 7.76-8.01 (m, 2H), 8.18-8.48 (m, 3H), 11.52 (s, 1H), 12.23 (s, 1H).

Workup

  1. customthe solvent was removed
  2. additionThe crude material was diluted with ethyl acetate
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cc6dd638957a4716a37444a0ce6fb22a
Source dataset
uspto-grants-2015_11
Patent number
US09181246B2

Reaction notes

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