Triethylsilane → HCID 86282041, compound

HRID 1052979Notes

Reaction equation

HRID 1052979 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(O)[C:17]2[CH:21]=[CH:20][S:19][CH:18]=2)=[C:5]([CH3:23])[O:4][N:3]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[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:21]=[CH:20][S:19][CH:18]=2)=[C:5]([CH3:23])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 86295676HCID 86295676, compound

Product 1

HCID 86282041HCID 86282041, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 5-(3,5-dimethylisoxazol-4-yl)-3-hydroxy-3-(thiophen-3-yl)indolin-2-one (50 mg, 0.153 mmol) in trifluoroacetic acid (10 mL) was added triethylsilane (5 mL). The brown solution was stirred at ambient temperature for 3 h and concentrated in vacuo to dryness. The residue was diluted with dichloromethane (20 mL), washed with saturated ammonium chloride solution (10 mL), brine (3×20 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was purified with chromatography on column to give the title compound (37 mg, 78.0%). 1H NMR (400 MHz, DMSO-d6): δH 10.62 (s, 1H), 7.53 (m, 1H), 7.31-7.32 (m, 1H), 7.22 (d, J=8.0 Hz, 1H), 7.16 (s, 1H), 7.02-7.03 (m, 1H), 6.97 (d, J=8.0 Hz, 1H), 4.90 (s, 1H), 2.35 (s, 3H), 2.18 (s, 3H). MS (ESI) m/e [M+1]+ 311.

Workup

  1. concentrationconcentrated in vacuo to dryness
  2. additionThe residue was diluted with dichloromethane (20 mL)
  3. washwashed with saturated ammonium chloride solution (10 mL), brine (3×20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo to dryness
  7. customThe residue was purified with chromatography on column

Sources & evidence

ORD record
ord-7fbaa665ef7f4e42b797f1966a2d7c20
Source dataset
uspto-grants-2016_07
Patent number
US09393232B2

Reaction notes

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