Tetrabutylammonium Fluoride → HCID 57562414, compound

HRID 1726059Notes

Reaction equation

HRID 1726059 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24]([N:26]1[C:34]2[C:29](=[CH:30][C:31]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:32][CH:33]=2)[C:28]([C:43]2[N:44]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[C:45]3[C:50]([CH:51]=2)=[CH:49][C:48]([O:52][SiH2]C(C)(C)C)=[CH:47][CH:46]=3)=[N:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>O1CCCC1>[C:19]([O:23][C:24]([N:26]1[C:34]2[C:29](=[CH:30][C:31]([O:35][CH2:36][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)=[CH:32][CH:33]=2)[C:28]([C:43]2[N:44]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[C:45]3[C:50]([CH:51]=2)=[CH:49][C:48]([OH:52])=[CH:47][CH:46]=3)=[N:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131727286Tert-butyl 3-[5-tert-butylsilyloxy-1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]-5-phenylmethoxyindazole-1-carboxylate

Product 1

HCID 57562414HCID 57562414, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.15 g of tetrabutylammonium fluoride are added to a solution of 13.4 g of 5-benzyloxy-3-(1-tert-butoxycarbonyl-5-tert-butylsilanyloxy-1H-indol-2-yl)-indazole-1-carboxylic acid tert-butyl ester in 140 ml of tetrahydrofuran. The medium is stirred for 30 minutes at ambient temperature. The reaction crude is washed with 3 times 25 ml of water, the organic phase is then dried over magnesium sulfate and then filtered, and the solvent is evaporated off under reduced pressure in a rotary evaporator. 14.4 g of crude product are obtained, which are purified by flash chromatography (silica 40-63 μm), eluent: dichloromethane/methanol 98:2 to obtain 8.54 g of 5-benzyloxy-3-(1-tert-butoxycarbonyl-5-hydroxy-1H-indol-2-yl)-indazole-1-carboxylic acid tert-butyl ester.

Workup

  1. customThe reaction crude
  2. washis washed with 3 times 25 ml of water
  3. dry with materialthe organic phase is then dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent is evaporated off under reduced pressure in a rotary evaporator
  6. custom14.4 g of crude product are obtained
  7. customwhich are purified by flash chromatography (silica 40-63 μm), eluent

Sources & evidence

ORD record
ord-eb33b722287c4784be16ce9ce890da82
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

Loading…