Propiolic Acid → Propynoic acid-(4'-chloro-3-fluorobiphenyl-4-yl)amide

HRID 734999Notes

Reaction equation

HRID 734999 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([F:15])[CH:9]=2)=[CH:4][CH:3]=1.[C:16](O)(=[O:19])[C:17]#[CH:18]>C1CCCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:16](=[O:19])[C:17]#[CH:18])=[C:10]([F:15])[CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10110Propiolic AcidHCID 200996184'-Chloro-3-fluoro[1,1'-biphenyl]-4-amine

Product 1

HCID 86060760Propynoic acid-(4'-chloro-3-fluorobiphenyl-4-yl)amide

Reagents, catalysts & solvents 1

HCID 21867204Cyclohexane ethylacetateSolvent

Procedure

Prepared analogously to Example 1.1.b. from 4′-chloro-3-fluorobiphenyl-4-ylamine and propynoic acid. Yield: 0.16 g (43.7% of theory); C15H9ClFNO (M=273.69); calc.: molecular ion peak (M+H)+: 274/276; found: molecular ion peak (M+H)+: 274/276; Rf value: 0.3 (silica gel, cyclohexane/ethyl acetate (3:1)).

Workup

  1. customPrepared analogously to Example 1.1.b

Sources & evidence

ORD record
ord-c2048dbe93a74a6caf66a26b1f236256
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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