Propionyl bromide → 4-(4-Bromo-2-fluorobenzyl)-3-n-butyl-1-[2-chloro-5-(propionylamino)phenyl]-1H-pyrazole-5-carbonitrile

HRID 257567Notes

Reaction equation

HRID 257567 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:28])=[C:6]([N:8]2[C:12]([C:13]#[N:14])=[C:11]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=3[F:23])[C:10]([CH2:24][CH2:25][CH2:26][CH3:27])=[N:9]2)[CH:7]=1.[C:29](Br)(=[O:32])[CH2:30][CH3:31]>CN(C1C=CN=CC=1)C>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][C:11]2[C:10]([CH2:24][CH2:25][CH2:26][CH3:27])=[N:9][N:8]([C:6]3[CH:7]=[C:2]([NH:1][C:29](=[O:32])[CH2:30][CH3:31])[CH:3]=[CH:4][C:5]=3[Cl:28])[C:12]=2[C:13]#[N:14])=[C:17]([F:23])[CH:18]=1

Participants

4

Reactant 2

HCID 69018Propionyl bromideHCID 197831511-(5-Amino-2-chlorophenyl)-4-(4-bromo-2-fluorobenzyl)-3-n-butyl-1H-pyrazole-5-carbonitrile

Product 1

HCID 197831434-(4-Bromo-2-fluorobenzyl)-3-n-butyl-1-[2-chloro-5-(propionylamino)phenyl]-1H-pyrazole-5-carbonitrileYield 73%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The acylation of 1-(5-amino-2-chlorophenyl)-4-(4-bromo-2-fluorobenzyl)-3-n-butyl-1H-pyrazole-5-carbonitrile (from Step G) with propionyl bromide in the presence of DMAP followed the procedure of Example 1, Step J. Flash chromatography of the crude product on silica gel (gradient elution with 5:1 to 3:1 hexane-EtOAc) afforded a 73% yield of the title compound as a tacky oil; homogeneous by TLC in 3:1 hexane-EtOAc; mass spectrum (FAB) m/e 517, 519 (M+1)+. 400 MHz 1H NMR (CDCl3) δ0.87 (t, J=7.3 Hz, 3H), 1.22 (t, J=7.6 Hz, 3H), 1.32 (m, 2H), 1.54 (m, 2H, partially obscured by H2O peak), 2.38 (q, J=7.6 Hz, 2H), 2.55 (t, J=7.8 Hz, 2H), 3.92 (s, 2H), 7.02 (dd, J≈8, 8.5 Hz, 1 H), 7.22-7.26 (m, 2H), 7.4-7.5 (m, 2H), 7.90 (d, J=2.2 Hz, 1H).

Sources & evidence

ORD record
ord-9e4b1fe7f8bd40738ff88dbaaf74cd67
Source dataset
uspto-grants-1993_11
Patent number
US05262412

Reaction notes

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