Water → 5-Chloro-3-{4-[(5-chloropyridin-2-yl)oxy]phenyl}pyridin-2-amine

HRID 1747925Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:9]=[CH:10][C:11](F)=[N:12][CH:13]=1.[NH2:15][C:16]1[C:21]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)=[CH:20][C:19]([Cl:29])=[CH:18][N:17]=1.O>CS(C)=O>[Cl:29][C:19]1[CH:20]=[C:21]([C:22]2[CH:23]=[CH:24][C:25]([O:28][C:11]3[CH:10]=[CH:9][C:8]([Cl:7])=[CH:13][N:12]=3)=[CH:26][CH:27]=2)[C:16]([NH2:15])=[N:17][CH:18]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of potassium carbonate (376 mg), 5-chloro-2-fluoropyridine (215 mg) and 4-(2-amino-5-chloropyridin-3-yl)phenol (300 mg) in DMSO (10 mL) was stirred at 120° C. for 5 hr. The mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed with 1N NaOH aq. and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane) to give the title compound (450 mg) as a pale yellow solid.

Workup

extractionextracted with EtOAc
customThe organic layer was separated
washwashed with 1N NaOH aq. and brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record: ord-4365a12c4bdc405b8763c95271c6f68b
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150591B2

Reaction notes

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