2-((4-(2-Fluoro-4-nitrophenoxy)quinolin-7-yl)oxy)-2-methylpropan-1-ol → 2-((4-(4-Amino-2-fluorophenoxy)quinolin-7-yl)oxy)-2-methylpropan-1-ol

HRID 2277397Notes

Reaction equation

[F:1][C:2]1[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][C:16]([CH3:20])([CH3:19])[CH2:17][OH:18])=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]=1.C(O[K])=O>C1COCC1.O.[Pd]>[NH2:25][C:23]1[CH:22]=[CH:21][C:3]([O:4][C:5]2[C:14]3[C:9](=[CH:10][C:11]([O:15][C:16]([CH3:20])([CH3:19])[CH2:17][OH:18])=[CH:12][CH:13]=3)[N:8]=[CH:7][CH:6]=2)=[C:2]([F:1])[CH:24]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 2-((4-(2-fluoro-4-nitrophenoxy)quinolin-7-yl)oxy)-2-methylpropan-1-ol (5.8 g, 15.6 mmol) in THF (23 mL) was added a solution of HCOOK (9.16 g, 10.9 mmol) in water (7.8 mL), followed by a catalytic amount of Pd/C (5%, 53%˜55% water content). The mixture was heated to 45° C. and stirred for 12 hours, and then filtered through a celite pad. The organic phase was separated, dried over Na2SO4 and concentrated in vacuo to afford a yellow foam solid. The title compound was purified by a silica gel chromatography (EtOAc/DCM=1/1) to give a light yellow solid (4.0 g, 75%).

Workup

filtrationfiltered through a celite pad
customThe organic phase was separated
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customto afford a yellow foam solid
customThe title compound was purified by a silica gel chromatography (EtOAc/DCM=1/1)

Sources & evidence

ORD record: ord-c8c0c8fe7b76442695bbda002f3ae61f
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133162B2

Reaction notes

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