HRID1726059

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID2724141

Tetra-n-butylammonium fluoride

C16H36FN

结构：CC(C)(C)OC(=O)n1nc(-c2cc3cc(O[SiH2]C(C)(C)C)ccc3n2C(=O)OC(C)(C)C)c2cc(OCc3ccccc3)ccc21

HCID131727286

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)n1nc(-c2cc3cc(O)ccc3n2C(=O)OC(C)(C)C)c2cc(OCc3ccccc3)ccc21

HCID57562414

未命名化合物

收率 73.6%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

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

后处理

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

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-eb33b722287c4784be16ce9ce890da82
来源数据集: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07491710B2
来源说明: uspto-grants-2009_02

反应 SMILES

[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]