Trifluoroacetic acid → 5-(1H-pyrrolo(2,3-b)pyridin-3-ylmethyl)-N-((4-(trifluoromethyl)phenyl)methyl)pyridin-2-amine

HRID 1782125Notes

Reaction equation

HRID 1782125 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]([C:12]2[CH:13]=[N:14][C:15]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)=[CH:16][CH:17]=2)O)=[CH:2]1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C.C(=O)(O)[O-].[Na+]>>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH2:10][C:12]2[CH:17]=[CH:16][C:15]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:22][CH:21]=3)=[N:14][CH:13]=2)=[CH:2]1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 57588067(1H-Pyrrolo[2,3-b]pyridin-3-yl)-[6-(4-trifluoromethyl-benzylamino)-pyridin-3-yl]-methanol

Product 1

HCID 115454195-(1H-pyrrolo(2,3-b)pyridin-3-ylmethyl)-N-((4-(trifluoromethyl)phenyl)methyl)pyridin-2-amineYield 62.8%

Procedure

Into a round bottom flask was added compound 14 (200.0 mg, 0.50 mmol) and trifluoroacetic acid (5.0 mL, 0.065 mol) and triethylsilane (3.0 mL, 0.019 mol). The reaction was stirred at room temperature for 30 min, poured into aqueous sodium bicarbonate, and the product was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified to give pure product 12 (Table 1 Cmpd 1-3) (120.0 mg, yield=62.8%) as a white solid (M+1=383).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-5f6417165d0346b58668bea51b35c166
Source dataset
uspto-grants-2009_03
Patent number
US07498342B2

Reaction notes

Loading…