HRID588111

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10898

2-Bromo-1-ethanol

C2H5BrO

HCID11430

Potassium Carbonate

CK2O3

反应SMILES：CC(=O)OCc1nc(Cl)cc2c1c(=O)[nH]n2C(c1ccccc1)(c1ccccc1)c1ccccc1

HCID118272544

未命名化合物

PRODUCTS

产物

反应SMILES：CC(=O)OCc1nc(Cl)cc2c1c(OCCO)nn2C(c1ccccc1)(c1ccccc1)c1ccccc1

HCID118271833

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

Dimethylformamide

C3H7NO

PROCEDURE

实验过程

A mixture of (6-chloro-3-oxo-1-trityl-2,3-dihydro-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl acetate (504.6 mg, 1.043 mmol) and potassium carbonate (558.3 mg, 4.04 mmol) in DMF (10 ml) was charged with 2-bromoethanol (0.30 ml, 4.25 mmol) and stirred at RT for 6 hr. Quenched with water and extracted 3× with Et2O. Washed organics with brine, dried over MgSO4, filtered and concentrated in vacuo. Purified via flash chromatography (0-100% EtOAc/Hex) to provide (6-chloro-3-(2-hydroxyethoxy)-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl acetate. MS: [M+H]+ m/z 528.

WORKUP

后处理

customQuenched with water
extractionextracted 3× with Et2O
dry with materialWashed organics with brine, dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurified via flash chromatography (0-100% EtOAc/Hex)

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-e7fbd7cc689b4b73b2451f2b3b91f1e2
来源数据集: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US09226922B2
来源说明: uspto-grants-2016_01

反应SMILES

[C:1]([O:4][CH2:5][C:6]1[C:11]2[C:12](=[O:34])[NH:13][N:14]([C:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]=2[CH:9]=[C:8]([Cl:35])[N:7]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:43][CH2:44][OH:45]>CN(C=O)C>[C:1]([O:4][CH2:5][C:6]1[C:11]2[C:12]([O:34][CH2:43][CH2:44][OH:45])=[N:13][N:14]([C:15]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]=2[CH:9]=[C:8]([Cl:35])[N:7]=1)(=[O:3])[CH3:2]