Tetrabutylammonium Fluoride → benzyl N-{2-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)-1H-indol-6-yl}-N-methylcarbamate

HRID 2068886Notes

Reaction equation

HRID 2068886 reaction equation
[CH3:1][C:2]1([CH3:48])[CH2:10][C:9]2[N:8](COCC[Si](C)(C)C)[N:7]=[C:6]([C:19]3[N:20](COCC[Si](C)(C)C)[C:21]4[C:26]([CH:27]=3)=[CH:25][CH:24]=[C:23]([N:28]([CH3:39])[C:29](=[O:38])[O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:22]=4)[C:5]=2[CH2:4][CH2:3]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O>[CH3:1][C:2]1([CH3:48])[CH2:10][C:9]2[NH:8][N:7]=[C:6]([C:19]3[NH:20][C:21]4[C:26]([CH:27]=3)=[CH:25][CH:24]=[C:23]([N:28]([CH3:39])[C:29](=[O:38])[O:30][CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:22]=4)[C:5]=2[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58550230benzyl N-(2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indol-6-yl)-N-methylcarbamate

Product 1

HCID 136127275benzyl N-{2-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)-1H-indol-6-yl}-N-methylcarbamateYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of benzyl N-(2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indol-6-yl)-N-methylcarbamate (13 g, 19 mmol) obtained in Example 1, Step 6, in N,N-dimethylformamide (102 ml) was added to tetrabutylammonium fluoride (93 ml, 93 mmol) concentrated in advance under reduced pressure, and then ethylenediamine (19 ml) was added. The mixture was stirred with heating at 90° C. for 7 hr. After cooling, water and ethyl acetate were added, and the organic layer was separated. Then, the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed successively with water, 10% aqueous citric acid solution and saturated brine, and dried over sodium sulfate. Sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography to give the title compound (7.2 g, yield 91%).

Workup

  1. concentrationconcentrated in advance under reduced pressure
  2. additionethylenediamine (19 ml) was added
  3. temperatureAfter cooling
  4. additionwater and ethyl acetate were added
  5. customthe organic layer was separated
  6. extractionThen, the aqueous layer was extracted with ethyl acetate
  7. washThe combined organic layers were washed successively with water, 10% aqueous citric acid solution and saturated brine
  8. dry with materialdried over sodium sulfate
  9. customSodium sulfate was removed by filtration
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f4be0872c0a64b54a3d430ebc168b899
Source dataset
uspto-grants-2012_10
Patent number
US08299070B2

Reaction notes

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