Stannous chloride dihydrate → HCID 23139463, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH3:20])[C:6]=1[C:7]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:8]=1[O:16][CH:17]([CH3:19])[CH3:18].O.O.Cl[Sn]Cl>>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH3:20])[C:6]=1[C:7]1[CH:12]=[C:11]([NH2:13])[CH:10]=[CH:9][C:8]=1[O:16][CH:17]([CH3:18])[CH3:19]Participants
3
Procedure
The crude reaction mixture of 4-bromo-5-(2-isopropoxy-5-nitro-phenyl)-1-methyl-1H-pyrazole (as described below) was reduced in the presence of SnCl2.2H2O, in a similar manner as described in Example 1.1, providing 3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-isopropoxy-phenylamine (0.043 g, 0.14 mmol, 50% for three steps). LCMS m/z (%)=310 (M+H79Br, 99), 312 (M+H81Br, 100). 1H NMR (400 MHz, CDCl3) δ: 7.51 (s, 1H), 6.89 (d, J=8.8 Hz, 1H), 6.76 (dd, J=2.7, 8.6 Hz, 1H), 6.62 (d, J=2.7 Hz, 1H), 4.08 (ddd, J=6.1, 6.1, 12.2 Hz, 1H), 3.74 (s, 3H), 1.21 (d, J=6.1 Hz, 3H), 1.01 (d, J=6.1 Hz, 3H).
Sources & evidence
- ORD record
- ord-b8af00dcfd07488b97829305d48fd916
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871797B2
Reaction notes
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