Trifluoroacetic acid → US9796708, Example 805

HRID 1522004Notes

Reaction equation

HRID 1522004 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([C:17]4[CH2:26][CH2:25][C:20]5(OCC[O:21]5)[CH2:19][CH:18]=4)=[CH:16][C:9]=23)[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([C:17]4[CH2:26][CH2:25][C:20](=[O:21])[CH2:19][CH:18]=4)=[CH:16][C:9]=23)[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 904120444-(5-fluoro-2-methoxyphenyl)-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 90413654US9796708, Example 805

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 241A (3.7 g, 9.73 mmol) in 30 mL dichloromethane was added excess trifluoroacetic acid (6 mL). The mixture was stirred at room temperature overnight and the solvent was removed in vacuo. The residue was dissolved in 50 mL ethyl acetate and washed with saturated sodium bicarbonate, water, and brine, dried over magnesium sulfate, filtered and concentrated. The crude material was triturated with ethyl acetate and the solid was filtered and dried in vacuo to give the title compound. MS (ESI): 337.2 (M+H)+.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in 50 mL ethyl acetate
  3. washwashed with saturated sodium bicarbonate, water, and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was triturated with ethyl acetate
  8. filtrationthe solid was filtered
  9. customdried in vacuo

Sources & evidence

ORD record
ord-caac27aaa8774a6cad7e8f7c32374cd7
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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