Reaction #577198

ord-1a5dcfb5600647a4b7ac5e22e5269b9e

Reaction equation

Nc1ccc(C(=O)c2ccc(F)cc2)cc1
4-amino-4′-fluorobenzophenone
[C-]#[C-]
Acetylide
[C-]#[C-].[Na+].[Na+]
sodium acetylide
Nc1ccc(C(=O)c2ccc(F)cc2)cc1
carbonyl
Nc1ccc(C(=O)c2ccc(F)cc2)cc1
4-amino-4′-fluorobenzophenone
C#CC(O)(c1ccc(N)cc1)c1ccc(F)cc1
1-(4-aminophenyl)-1-(4-fluorophenyl)-2-propyn-1-ol

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Referring now to FIG. 2, wherein one non-limiting approach to the 1-(4-aminophenyl)-1-(4-fluorophenyl)-2-propyn-1-ol is presented, 4,4′-difluorobenzophenone (7) is reacted with a secondary amine HNR′″R″″ to give the 4-amino-4′-fluorobenzophenone 8, where R′″ and R″″ may be the same as R36 and R37, respectively, as set forth and claimed herein. Acetylide anion, for example, sodium acetylide in acetylene saturated dimethylformamide, is added to the carbonyl of 4-amino-4′-fluorobenzophenone 8 to give, upon aqueous workup, 1-(4-aminophenyl)-1-(4-fluorophenyl)-2-propyn-1-ol 9.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07527754B2uspto-grants-2009_05