Trifluoroacetic acid → HCID 86282035, compound

HRID 1052970Notes

Reaction equation

HRID 1052970 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[C:10]3(NCCO)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:5]([CH3:27])[O:4][N:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[CH:10]3[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:5]([CH3:27])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86280820HCID 86280820, compound

Product 1

HCID 86282035HCID 86282035, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(3,5-dimethylisoxazol-4-yl)-3-(2-hydroxyethylamino)-3-phenylindolin-2-one (32 g, 0.1 mmol) in dichloromethane (500 mL) was added trifluoroacetic acid (20 g) and triethylsilane (20 g). The brown solution was stirred at ambient temperature for 3 h and concentrated in vacuo to dryness. The residue was diluted with dichloromethane (500 mL), washed with saturated ammonium chloride solution (200 mL), brine (3×400 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was crystallized from ether to give the title compound. 1H NMR (400 MHz, DMSO-d6): δH 10.63 (s, 1H), 7.18-7.36 (m, 6H), 6.99-7.04 (m, 2H), 4.82 (s, 1H), 2.32 (s, 3H), 2.15 (s, 3H). MS (ESI) m/e [M+1]+ 305.

Workup

  1. concentrationconcentrated in vacuo to dryness
  2. additionThe residue was diluted with dichloromethane (500 mL)
  3. washwashed with saturated ammonium chloride solution (200 mL), brine (3×400 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo to dryness
  7. customThe residue was crystallized from ether

Sources & evidence

ORD record
ord-6ade0370794b41d7ba1f35ea502bafb1
Source dataset
uspto-grants-2016_07
Patent number
US09393232B2

Reaction notes

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