Potassium Carbonate → 3-Bromo-4-[(5-chloro-6-isopropoxypyridin-3-yl)oxy]benzonitrile

HRID 1620339Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[Br:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1F)[C:17]#[N:18].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Br:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[O:12][C:4]1[CH:5]=[N:6][C:7]([O:8][CH:9]([CH3:10])[CH3:11])=[C:2]([Cl:1])[CH:3]=1)[C:17]#[N:18]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 5-chloro-6-isopropoxypyridin-3-ol (Preparation 35, 350 mg, 1.87 mmol) in dimethyl sulfoxide (2 mL) was added 3-bromo-4-fluorobenzonitrile (333 mg, 1.87 mmol) and potassium carbonate (386 mg, 2.80 mmol). The reaction was stirred at 50° C. for 4 hours and then partitioned between water (100 mL) and EtOAc. The aqueous phase was separated and extracted with EtOAc (2×25 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a colourless oil which crystallised on standing (920 mg) and which was used without further purification in the next step.

Workup

custompartitioned between water (100 mL) and EtOAc
customThe aqueous phase was separated
extractionextracted with EtOAc (2×25 mL)
dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-156dc03988cf44788d05b5fbaae6ef4f
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772343B2

Reaction notes

Loading…