Stannous chloride dihydrate → HCID 23139445, compound

HRID 919438Notes

Reaction equation

HRID 919438 reaction equation
[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[CH:16][C:9]=1[O:10][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14].O.O.Cl[Sn]Cl>CCO>[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:19]=[C:18]([NH2:20])[CH:17]=[CH:16][C:9]=1[O:10][CH2:11][CH2:12][N:13]([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 23139512HCID 23139512, compound

Product 1

HCID 23139445HCID 23139445, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

{2-[2-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-4-nitro-phenoxy]-ethyl}-dimethyl-amine (0.128 g, 0.35 mmol) was treated with SnCl2.2H2O (0.319 g, 1.39 mmol, 4.0 equiv.) in EtOH (20 mL), in a similar manner as described in Example 1.1, providing 3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-(2-dimethylamino-ethoxy)-phenylamine (0.067 g, 0.20 mmol, 56%) as an oil. LCMS m/z (%)=339 (M+H79Br, 78), 341 (M+H81Br, 100). 1H NMR (400 MHz, acetone-d6) δ: 7.68 (dd, J=2.5, 8.9 Hz, 1H), 7.55 (s, 1H), 7.45-7.51 (m, 2H), 4.62-4.82 (m, 2H), 3.76 (s, 3H), 3.65-3.76 (m, 2H), 2.87 (s, 6H). The intermediate {2-[2-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-nitro-phenoxy]-ethyl}-dimethyl-amine was prepared in the following manner:

Sources & evidence

ORD record
ord-a421934efd534912a54b2ce6e9ca9800
Source dataset
uspto-grants-2016_03
Patent number
US09273035B2

Reaction notes

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