Water → 5-Bromo-2-(4-methoxyphenyl)pyridine

HRID 1047066Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[N:6][CH:7]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+].O>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-bromo-2-iodopyridine (600 mg, 2.11 mmol), (4-methoxyphenyl)boronic acid (353 mg, 2.32 mmol), tetrakis(triphenylphosphine)palladium(0) (122 mg, 0.106 mmol), and 2M Na2CO3 aq. (2.11 mL, 4.22 mmol) in toluene (10 mL) was heated at 80° C. for 40.5 hours under nitrogen. After cooling to room temperature, water was added and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and filtered through a Celite pad. The filtrate was concentrated and the residue was purified by column chromatography (CH2Cl2 only) to afford the desired product (538 mg, 97%) as a yellow solid. 1HNMR (CDCl3) 400 MHz δ: 8.69 (d, J=2.3 Hz, 1H), 7.92 (dt, J=8.6 Hz and 2.3 Hz, 2H), 7.82 (dd, J=8.6 Hz and 2.3 Hz, 1H), 7.56 (d, J=8.6 Hz, 1H), 6.99 (dt, J=8.6 Hz and 2.3 Hz, 2H), 3.87 (s, 3H). LCMS: 264 [M+H].

Workup

temperatureAfter cooling to room temperature
extractionextracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered through a Celite pad
concentrationThe filtrate was concentrated
customthe residue was purified by column chromatography (CH2Cl2 only)

Sources & evidence

ORD record: ord-f3bb9c65e3c8421fa7262e5a3a9acf2c
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569331B2

Reaction notes

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