1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate → HCID 136342068, compound

HRID 1726103Notes

Reaction equation

HRID 1726103 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:15]=2)[C:10]([C:25]2[N:26]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[C:29]([O:34][Si](C(C)(C)C)(C)C)[CH:28]=3)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.ClCCl>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:14][CH:15]=2)[C:10]([C:25]2[N:26]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[C:29]([OH:34])[CH:28]=3)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 68838712HCID 68838712, compound

Product 1

HCID 136342068HCID 136342068, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.50 g of 5-benzyloxy-3-[1-tert-butoxycarbonyl-6-(tert-butyldimethyl-silanyloxy)-1H-indol-2-yl]indazole-1-carboxylic acid tert-butyl ester in solution in 35 ml of tetrahydrofuran with 770 mg of tetrabutylammonium fluoride hydrate are stirred at ambient temperature. After stirring for 1 h 30 min, the medium is diluted with dichloromethane and the organic phase is then washed with distilled water. After drying over magnesium sulfate and filtration, the solvent is evaporated off under vacuum in a rotary evaporator to obtain 1.05 g of 5-benzyloxy-3-(1-tert-butoxycarbonyl-6-hydroxy-1H-indol-2-yl)indazole-1-carboxylic acid tert-butyl ester.

Workup

  1. washthe organic phase is then washed with distilled water
  2. dry with materialAfter drying over magnesium sulfate and filtration
  3. customthe solvent is evaporated off under vacuum in a rotary evaporator

Sources & evidence

ORD record
ord-5b738bb6fca441cab9b4e1b06ac99081
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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