Tetrabutylammonium Fluoride → HCID 178517043, compound

HRID 1615313Notes

Reaction equation

HRID 1615313 reaction equation
[CH:1]1([C:4]2[C:12]3[C:7](=[CH:8][C:9](/[CH:13]=[C:14]4/[C:15](=[O:23])[NH:16][C:17]5[C:22]/4=[CH:21][CH:20]=[CH:19][CH:18]=5)=[CH:10][CH:11]=3)[N:6](COCC[Si](C)(C)C)[N:5]=2)[CH2:3][CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH:1]1([C:4]2[C:12]3[C:7](=[CH:8][C:9](/[CH:13]=[C:14]4/[C:15](=[O:23])[NH:16][C:17]5[C:22]/4=[CH:21][CH:20]=[CH:19][CH:18]=5)=[CH:10][CH:11]=3)[NH:6][N:5]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68753876HCID 68753876, compound

Product 1

HCID 178517043HCID 178517043, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (E)-3-((3-cyclopropyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-6-yl)methylene)indolin-2-one (47 mg, 0.11 mmol) and tetrabutylammonium fluoride (1.0 M in THF, 10 mL, 10 mmol) in anh. THF (30 mL) was refluxed under Ar for 18 h. The reaction mixture was then concentrated to a brown oil, which was diluted with H2O, extracted (2% MeOH in DCM), washed (H2O (2×), brine), dried (Na2SO4, and MgSO4) and concentrated under reduced pressure. The material was suspended in DCM, collected by filtration and washed with xs. DCM to afford the title compound as a yellow solid (7.0 mg, 21%). 1H NMR (400 MHz, CD3OD) δ ppm 7.90 (d, J=8.53 Hz, 1H), 7.86 (s, 1H), 7.78 (s., 1H), 7.65 (d, J=8.03 Hz, 1H), 7.42 (d, J=8.78 Hz, 1H), 7.23 (t, J=8.03 Hz, 1H), 6.92 (d, J=7.78 Hz, 1H), 1H), 6.87 (t, J=7.65 Hz, 1H), 2.26-2.36 (m, 1H), 1.04-1.11 (m, 4H); MS ESI 302.1 [M+H]+, calcd for [C19H15N3O+H]+ 302.3.

Workup

  1. temperaturewas refluxed under Ar for 18 h
  2. concentrationThe reaction mixture was then concentrated to a brown oil, which
  3. additionwas diluted with H2O
  4. extractionextracted (2% MeOH in DCM)
  5. washwashed (H2O (2×), brine)
  6. dry with materialdried (Na2SO4, and MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. filtrationcollected by filtration
  9. washwashed with xs

Sources & evidence

ORD record
ord-bf0a63c13d6c40d281b6e9fd713c7305
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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