4-(4-Bromo-2-fluorobenzyl)-3-n-butyl-1-(2-chloro-5-nitrophenyl)-1H-pyrazole-5-carbonitrile → 1-(5-Amino-2-chlorophenyl)-4-(4-bromo-2-fluorobenzyl)-3-n-butyl-1H-pyrazole-5-carbonitrile

HRID 257566Notes

Reaction equation

HRID 257566 reaction equation
[Br:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][C:7]2[C:8]([CH2:24][CH2:25][CH2:26][CH3:27])=[N:9][N:10]([C:14]3[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[CH:16][C:15]=3[Cl:23])[C:11]=2[C:12]#[N:13])=[C:4]([F:30])[CH:3]=1>[Pt]=O>[NH2:20][C:18]1[CH:17]=[CH:16][C:15]([Cl:23])=[C:14]([N:10]2[C:11]([C:12]#[N:13])=[C:7]([CH2:6][C:5]3[CH:28]=[CH:29][C:2]([Br:1])=[CH:3][C:4]=3[F:30])[C:8]([CH2:24][CH2:25][CH2:26][CH3:27])=[N:9]2)[CH:19]=1

Participants

3

Reactant 1

HCID 197832514-(4-Bromo-2-fluorobenzyl)-3-n-butyl-1-(2-chloro-5-nitrophenyl)-1H-pyrazole-5-carbonitrile

Product 1

HCID 197831511-(5-Amino-2-chlorophenyl)-4-(4-bromo-2-fluorobenzyl)-3-n-butyl-1H-pyrazole-5-carbonitrileYield 96%

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

By the procedure of Example 1, Step I, 4-(4-bromo-2-fluorobenzyl)-3-n-butyl-1-(2-chloro-5-nitrophenyl)-1H-pyrazole-5-carbonitrile (from Step F) was hydrogenated in the presence of platinum oxide catalyst to give a 96% yield of the title compound as a tacky, orange oil; nearly homogeneous by TLC in 3:1 hexane-EtOAc; mass spectrum (FAB) m/e 461, 463 (M+1)+. 200 MHz 1H NMR (CDCl3) δ0.89 (t, J=7.2 Hz, 3H), 1.33 (m, 2H), 1.58 (m, 2H), 2.58 (t, J=7.7 Hz, 2H), 3.94 (s, 2H), 6.69-6.75 (m, 2H), 7.03 (dd, J≈8, 8.5 Hz, 1H), 7.2-7.3 (m, 3H).

Sources & evidence

ORD record
ord-9c822bdf0b574a5480dfde01d9d7e044
Source dataset
uspto-grants-1993_11
Patent number
US05262412

Reaction notes

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