HRID627802

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID2724141

Tetra-n-butylammonium fluoride

C16H36FN

结构：CC(C)S(=O)(=O)c1ccc(-c2cnc3c(n2)c(N2C(=O)c4ccccc4C2CCO[Si](C)(C)C(C)(C)C)cn3C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1

HCID71143650

未命名化合物

PRODUCTS

生成物

结构：CC(C)S(=O)(=O)c1ccc(-c2cnc3c(n2)c(N2C(=O)c4ccccc4C2CCO)cn3C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1

HCID71143611

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

3 次

PROCEDURE

实验过程

3-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-2-[2-(4-isopropylsulfonylphenyl)-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl]isoindolin-1-one (123 mg, 0.1476 mmol) dissolved in THF (2 mL) under N2. TBAF in THF (442.8 μL of 1.0 M, 0.4428 mmol) in THF added and the mixture stirred for 90 mins. Reaction mixture partitioned between DCM and brine. Aqueous phase extracted with DCM and combined organics dried and concentrated. Residue purified by chromatography (silica, 0-100% EtOAc-petrol gradient). Title compound obtained as a yellow film, (87 mg, 82%), taken on directly to deprotection reaction; MS (ES+) 719.0.

WORKUP

后处理

customReaction mixture
custompartitioned between DCM and brine
extractionAqueous phase extracted with DCM
customcombined organics dried
concentrationconcentrated
customResidue purified by chromatography (silica, 0-100% EtOAc-petrol gradient)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-04d32ebf7ab342cf8a4356dcc2adb40f
来源数据集: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09309250B2
来源说明: uspto-grants-2016_04

反应 SMILES

[Si]([O:8][CH2:9][CH2:10][CH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:20])[N:12]1[C:21]1[C:29]2[C:24](=[N:25][CH:26]=[C:27]([C:30]3[CH:35]=[CH:34][C:33]([S:36]([CH:39]([CH3:41])[CH3:40])(=[O:38])=[O:37])=[CH:32][CH:31]=3)[N:28]=2)[N:23]([C:42]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:22]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH2:9][CH2:10][CH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:20])[N:12]1[C:21]1[C:29]2[C:24](=[N:25][CH:26]=[C:27]([C:30]3[CH:35]=[CH:34][C:33]([S:36]([CH:39]([CH3:40])[CH3:41])(=[O:38])=[O:37])=[CH:32][CH:31]=3)[N:28]=2)[N:23]([C:42]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[CH:22]=1