Tetrabutylammonium Fluoride → HCID 178517056, compound

HRID 1615318Notes

Reaction equation

HRID 1615318 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1/[CH:7]=[CH:8]/[C:9]1[C:17]2[C:12](=[CH:13][C:14](/[CH:18]=[C:19]3/[C:20](=[O:28])[NH:21][C:22]4[C:27]/3=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:15][CH:16]=2)[N:11](COCC[Si](C)(C)C)[N:10]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1/[CH:7]=[CH:8]/[C:9]1[C:17]2[C:12](=[CH:13][C:14]([CH:18]=[C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][C:20]3=[O:28])=[CH:15][CH:16]=2)[NH:11][N:10]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68756554HCID 68756554, compound

Product 1

HCID 178517056HCID 178517056, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A degassed mixture of (E)-3-((3-((E)-2-(pyrazin-2-yl)vinyl)-1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-indazol-6-yl)methylene)indolin-2-one (20 mg, 0.040 mmol) and tetrabutylammonium fluoride (1.0 M in THF, 0.6 mL, 0.6 mmol) in anh. THF (10 mL) was refluxed under Ar for 1 d. The reaction mixture was then concentrated under reduced pressure and purified by prepTLC (SiO2 12% MeOH/DCM) and trituration with DCM to provide the title compound as a 1.5:1.0 (E:Z) mixture of isomers: a yellow solid (1.7 mg, 12%). 1H NMR (400 MHz, DMF-d7) δ ppm 9.33 (s, 0.35H), 9.16 (d, J=1.51 Hz, 1.0H), 8.84-8.87 (m, 1.1H), 8.70 (t, J=2.26 Hz, 1.0H), 8.60 (d, J=8.78 Hz, 0.6H), 8.51 (d, J=8.28 Hz, 0.45H), 8.37-8.46 (m, 1.6H), 8.26 (d, J=5.52 Hz, 1.0H), 8.04 (s, 0.6H), 8.02 (d, J=7.53 Hz, 0.39H), 7.92-7.98 (m, 1.7H), 7.79 (d, J=8.03 Hz, 0.60H), 7.41-7.49 (m, 1.1H), 7.05-7.25 (m, 2.1H); MS ESI 366.2 [M+H]+, calcd for [C22H15N5O+H]+ 366.4.

Workup

  1. temperaturewas refluxed under Ar for 1 d
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. custompurified by prepTLC (SiO2 12% MeOH/DCM) and trituration with DCM

Sources & evidence

ORD record
ord-e37096bee5394d3e8a8e149c2a950f8c
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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