Tetrabutylammonium Fluoride → HCID 136127223, compound

HRID 2068893Notes

Reaction equation

HRID 2068893 reaction equation
[Si]([O:18][CH2:19][CH:20]([N:22]([CH3:61])[C:23]([C:25]1[CH:33]=[C:32]2[C:28]([CH:29]=[C:30]([C:42]3[C:50]4[CH2:49][CH2:48][C:47]([CH3:52])([CH3:51])[CH2:46][C:45]=4[N:44](COCC[Si](C)(C)C)[N:43]=3)[N:31]2COCC[Si](C)(C)C)=[CH:27][CH:26]=1)=[O:24])[CH3:21])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O>[OH:18][CH2:19][CH:20]([N:22]([CH3:61])[C:23]([C:25]1[CH:33]=[C:32]2[C:28]([CH:29]=[C:30]([C:42]3[C:50]4[CH2:49][CH2:48][C:47]([CH3:52])([CH3:51])[CH2:46][C:45]=4[NH:44][N:43]=3)[NH:31]2)=[CH:27][CH:26]=1)=[O:24])[CH3:21]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58550183HCID 58550183, compound

Product 1

HCID 136127223HCID 136127223, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indole-6-carboxylic acid [2-(tert-butyldiphenylsilyloxy)-1-methylethyl]methylamide (145 mg, 0.17 mmol) in N,N-dimethylformamide (1.2 ml) was added to tetrabutylammonium fluoride (1.7 ml, 1.7 mmol) concentrated in advance under reduced pressure. Ethylenediamine (0.29 ml) was added, and the mixture was stirred with heating at 90° C. for 14 hr. After cooling, to the mixture were added water and ethyl acetate, and the organic layer was separated, 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 (57 mg, yield 90%).

Workup

  1. concentrationconcentrated in advance under reduced pressure
  2. additionEthylenediamine (0.29 ml) was added
  3. temperatureAfter cooling, to the mixture
  4. additionwere added water and ethyl acetate
  5. customthe organic layer was separated
  6. washwashed successively with water, 10% aqueous citric acid solution and saturated brine
  7. dry with materialdried over sodium sulfate
  8. customSodium sulfate was removed by filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9b6474aefd0b43d297999ef6d763071b
Source dataset
uspto-grants-2012_10
Patent number
US08299070B2

Reaction notes

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