4-Iodobenzyl alcohol → 3-(4-Hydroxymethylphenyl)propynoic acid-(4'-chlorobiphenyl-4-yl)methylamide

HRID 735003Notes

Reaction equation

HRID 735003 reaction equation
I[C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][NH:24][C:25](=[O:28])[C:26]#[CH:27])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1.ClCCl.CO.N>>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][NH:24][C:25](=[O:28])[C:26]#[C:27][C:2]3[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=3)=[CH:19][CH:18]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 290124-Iodobenzyl alcoholHCID 21584172Ammonia methanol dichloromethaneHCID 86047930Propynoic acid-(4'-chlorobiphenyl-4-yl)methylamide

Product 1

HCID 688195973-(4-Hydroxymethylphenyl)propynoic acid-(4'-chlorobiphenyl-4-yl)methylamide

Procedure

Prepared analogously to Example 1.2.a. from 4-iodobenzyl alcohol and propynoic acid-(4′-chlorobiphenyl-4-yl)methylamide. Yield: 0.52 g (90% of theory); C23H18ClNO2 (M=375.85); calc.: molecular ion peak (M+H)+: 376/378; found: molecular ion peak (M+H)+: 376/378; Rf value: 0.4 (silica gel, dichloromethane/methanol/ammonia (10:1:0.1)).

Workup

  1. customPrepared analogously to Example 1.2.a

Sources & evidence

ORD record
ord-53c4889e70674dea8a0c2cd8450c4ea6
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

Loading…