Stannous chloride dihydrate → HCID 23139455, compound

HRID 407399Notes

Reaction equation

HRID 407399 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=1[C:18]1[N:22]([CH3:23])[N:21]=[CH:20][C:19]=1[Br:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.Cl[Sn]Cl>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=1[C:18]1[N:22]([CH3:23])[N:21]=[CH:20][C:19]=1[Br:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 23139464HCID 23139464, compound

Product 1

HCID 23139455HCID 23139455, compoundYield 39%

Procedure

The reaction mixture of 5-(2-benzyloxy-5-nitro-phenyl)-4-bromo-1-methyl-1H-pyrazole was reduced in the presence of SnCl2.2H2O, in a similar manner as described in Example 1. 1, providing 4-benzyloxy-3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-phenylamine (0.079 g, 0.22 mmol, 39% for three steps). LCMS m/z (%)=358 (M+H79Br, 98), 360 (M+H81Br, 100). 1H NMR (400 MHz, CDCl3) δ: 7.45 (s, 1H), 7.15-7.26 (m, 3H), 7.10 (d, J=6.6 Hz, 2H), 6.83 (d, J=8.7 Hz, 1H), 6.66 (dd, J=2.8, 8.6 Hz, 1H), 6.55 (d, J=2.8 Hz, 1H), 4.83 (AB quartet, J=12.0, 17.2 Hz, 2H), 3.62 (s, 3H).

Sources & evidence

ORD record
ord-04c63b268a2e4257a75d22254351239e
Source dataset
uspto-grants-2014_06
Patent number
US08754238B2

Reaction notes

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