Stannous chloride dihydrate → 5-((1-Methyl-1H-pyrazol-3-yl)methoxy)-N1-(2-methyl-4-(trifluoromethoxy)benzyl)benzene-1,2-diamine

HRID 1527752Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([N+:29]([O-])=O)=[C:13]([CH:28]=2)[NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][C:17]=2[CH3:27])=[N:3]1.O.O.Cl[Sn]Cl>C(O)C.C([O-])(O)=O.[Na+]>[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:28]=[C:13]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:24])([F:25])[F:26])=[CH:18][C:17]=3[CH3:27])[C:12]([NH2:29])=[CH:11][CH:10]=2)=[N:3]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of 5-((1-methyl-1H-pyrazol-3-yl)methoxy)-N-(2-methyl-4-(trifluoromethoxy)benzyl)-2-nitroaniline (187 mg, 0.43 mmol) in ethanol (30 mL) was added SnCl2.2H2O (482 mg, 2.21 mmol). The resulting mixture was heated at 90° Celsius. After overnight, the mixture was cooled to RT and diluted with saturated NaHCO3 (40 mL). The resulting mixture was extracted with DCM (3×50 mL). The combined organics were concentrated to dryness to provide the title compound, which was used without further purification. MS (ESI): mass calcd. for C20H21F3N4O2, 406.16; m/z found, 407 [M+H]+.

Workup

temperaturethe mixture was cooled to RT
extractionThe resulting mixture was extracted with DCM (3×50 mL)
concentrationThe combined organics were concentrated to dryness

Sources & evidence

ORD record: ord-e53ee034ee96409b816d5d1406ab4647
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09089569B2

Reaction notes

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