1,2-Dichloroethane → 3, 4, 5-tris(benzyloxy)-N-(2-(5-methoxy-1H-indol-3-yl)ethyl)benzamide

HRID 1398726Notes

Reaction equation

HRID 1398726 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:34][O:35][C:36]1[CH:47]=[C:46]2[C:39]([NH:40][CH:41]=[C:42]2[CH2:43][CH2:44][NH2:45])=[CH:38][CH:37]=1.C(Cl)CCl.CO>C(Cl)(Cl)Cl>[CH2:27]([O:26][C:16]1[CH:15]=[C:11]([CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:17]=1[O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:12]([NH:45][CH2:44][CH2:43][C:42]1[C:46]2[C:39](=[CH:38][CH:37]=[C:36]([O:35][CH3:34])[CH:47]=2)[NH:40][CH:41]=1)=[O:14])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 887MethanolHCID 18335-MethoxytryptamineHCID 111339693,4,5-Tris(benzyloxy)benzoic Acid

Product 1

HCID 668035523, 4, 5-tris(benzyloxy)-N-(2-(5-methoxy-1H-indol-3-yl)ethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2g was synthesized by the condensation of 1b (480 mg, 1.09 mmol) and 5-methoxy tryptamine (248 mg, 1.308 mmol) using standard EDC coupling method and was isolated as white solid (565 mg, 84%) by elution with 0.5% methanol in chloroform. Rf: 0.517 (1.6% methanol in chloroform); mp: 125-128° C.;

Sources & evidence

ORD record
ord-a62e7664cfa34ab39b95f9aa5ba3ae5c
Source dataset
uspto-grants-2014_12
Patent number
US08901317B2

Reaction notes

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