Triethylamine → 5-(5-Methoxy-benzofuran-2-yl)-pyridin-2-ol

HRID 501040Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9](B(O)O)=[CH:8][C:7]=2[CH:14]=1.I[C:16]1[CH:17]=[CH:18][C:19](=[O:22])[NH:20][CH:21]=1.CCN(CC)CC>CCO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:16]3[CH:17]=[CH:18][C:19]([OH:22])=[N:20][CH:21]=3)=[CH:8][C:7]=2[CH:14]=1

Participants

Conditions

Temperature: 140 °C

Procedure

5-methoxybenzofuran boronic acid (230 mg, 1.2 mmol), 5-iodo-2-pyridone (221 mg, 1.0 mmol), Pd(PPh3)2Cl2 (17 mg, 0.024 mmol) and NEt3 (317 μL, 2.4 mmol) were mixed in EtOH (10 mL) in a 20 mL microwave vial. The mixture was stirred at 140° C. for 10 min in a microwave reactor. The solvent was removed under vacuum, water was added and the solution was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and the solvent removed under vacuum. The crude substance was purified by preparative HPLC to afford the title compound as a white solid (20 mg). 1H NMR δ ppm 11.95 (br. s., 1 H) 7.94 (dd, 1 H) 7.88 (s, 1 H) 7.44 (d, 1 H) 7.00-7.20 (m, 2 H) 6.84 (dd, 1 H) 6.48 (d, 1H) 3.78 (s, 3 H); MS m/z 242 (M+H).

Workup

customThe solvent was removed under vacuum, water
additionwas added
extractionthe solution was extracted with EtOAc
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
customthe solvent removed under vacuum
customThe crude substance was purified by preparative HPLC

Sources & evidence

ORD record: ord-0eec50132b5c400597368b4f725acea8
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772256B2

Reaction notes

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