HRID1274407

反应详情

EQUATION

反应方程式

REACTANTS

反应物

反应SMILES：CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]

HCID5049666

Sodium triacetoxyborohydride

C6H10BNaO6

HCID22120673

未命名化合物

反应SMILES：Cc1cc(C)cc(-c2[nH]c3ccc(C(=O)N(CC(C)C)CC(C)C)cc3c2CCN)c1

HCID53794651

未命名化合物

PRODUCTS

产物

反应SMILES：Cc1cc(C)cc(-c2[nH]c3ccc(C(=O)N(CC(C)C)CC(C)C)cc3c2CCN(CCCCc2ccnc3cc(Cl)ccc23)CCCCc2ccnc3cc(Cl)ccc23)c1

HCID53858247

未命名化合物

收率 23.8%

PROCEDURE

实验过程

To a solution of 3-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid diisobutylamide (89 mg in 3.0 mL dry tetrahydrofuran) at 0° C. was added 50 mg 4-(7-chloroquinolin-4-yl)butyraldehyde and the mixture stirred for 10 minutes. At this time, 67.4 mg sodium triacetoxyborohydride were added and the mixture allowed to warm slowly to room temperature. After 5 hours, the reaction was quenched by the addition of brine and the mixture extracted with methylene chloride. The combined organics were dried over sodium sulfate and the concentrate purified by preparative tlc on silica gel (methylene chloride:methanol, 95:5) to give the title compound (21.8 mg).

WORKUP

后处理

waitAfter 5 hours
customthe reaction was quenched by the addition of brine
extractionthe mixture extracted with methylene chloride
dry with materialThe combined organics were dried over sodium sulfate
customthe concentrate purified by preparative tlc on silica gel (methylene chloride:methanol, 95:5)

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-17f5b6d374ff43fcb4cec6c10174f08b
来源数据集: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US06156767
来源说明: uspto-grants-2000_12

反应SMILES

[CH2:1]([N:5]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:6]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=1)=[C:11]2[CH2:25][CH2:26][NH2:27])=[O:7])[CH:2]([CH3:4])[CH3:3].[Cl:32][C:33]1[CH:42]=[C:41]2[C:36]([C:37]([CH2:43][CH2:44][CH2:45][CH:46]=O)=[CH:38][CH:39]=[N:40]2)=[CH:35][CH:34]=1.C(O[BH-](O[C:58](=O)[CH3:59])OC(=O)C)(=O)C.[Na+]>>[CH2:1]([N:5]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:6]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]1[CH:18]=[C:19]([CH3:24])[CH:20]=[C:21]([CH3:23])[CH:22]=1)=[C:11]2[CH2:25][CH2:26][N:27]([CH2:46][CH2:45][CH2:44][CH2:43][C:37]1[C:58]2[C:59](=[CH:42][C:33]([Cl:32])=[CH:34][CH:35]=2)[N:40]=[CH:39][CH:38]=1)[CH2:46][CH2:45][CH2:44][CH2:43][C:37]1[C:36]2[C:41](=[CH:42][C:33]([Cl:32])=[CH:34][CH:35]=2)[N:40]=[CH:39][CH:38]=1)=[O:7])[CH:2]([CH3:4])[CH3:3]