4-Bromobenzylamine → N-(4-Bromobenzyl)-5-((5-methylpyridin-2-yl)methoxy)-2-nitroaniline

HRID 1848708Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-((3-fluoro-4-nitrophenoxy)methyl)-5-methylpyridine (2.0 g, 7.6 mmol), 4-bromobenzyl amine (1.6 g, 8.4 mmol), DIPEA (2.63 mL, 15.3 mmol) and acetonitrile (25.4 mL) were sealed in a reaction vessel and heated to 60° Celsius for 24 h. The mixture was cooled to RT, transferred to a round bottomed flask and concentrated to dryness. The crude mixture was heated to 70° Celsius in a minimum amount of i-PrOH until homogeneous and cooled to RT. The resulting mixture was filtered to collect the yellow solids which were dried to afford the title compound (2.82 g, 86%). MS (ESI): mass calcd. for C20H18BrN3O3, 427.053; m/z found, 428.0 [M+H]+.

Workup

customwere sealed in a reaction vessel
temperatureThe mixture was cooled to RT
customtransferred to a round bottomed flask
concentrationconcentrated to dryness
temperatureThe crude mixture was heated to 70° Celsius in a minimum amount of i-PrOH until homogeneous and
temperaturecooled to RT
filtrationThe resulting mixture was filtered
customto collect the yellow solids which
customwere dried

Sources & evidence

ORD record: ord-b886f18200164e86a4cf797a9c60e2e2
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952177B2

Reaction notes

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