Triethylamine → 5-(5-methoxy-1-benzofuran-2-yl)-N-methyl-2-pyridinamine

HRID 501045Notes

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.Br[C:16]1[CH:17]=[CH:18][C:19](CN)=[N:20][CH:21]=1.C[CH2:25][N:26](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]([NH:26][CH3:25])=[N:20][CH:21]=3)=[CH:8][C:7]=2[CH:14]=1

Participants

Conditions

Temperature: 140 °C

Procedure

5-methoxybenzofuran boronic acid (1.2 mmol), 5-bromopyridine-2-methylamine (1.0 mmol), Pd(PPh3)2Cl2 (0.024 mmol) and NEt3 (317 μL) 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 concentrated under vacuum. The crude substance was purified by preparative HPLC to afford the title compound as a white solid (100 mg). 1H NMR δ ppm 8.53 (d, 1 H) 7.84 (dd, 1 H) 7.44 (d, 1 H) 7.08 (d, 1 H) 7.04 (s, 1 H) 6.91 (d, 1 H) 6.81 (dd, 1 H) 6.55 (d, 1 H) 3.78 (s, 3 H) 2.83 (d, 3 H); MS m/z 255 (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
concentrationconcentrated under vacuum
customThe crude substance was purified by preparative HPLC

Sources & evidence

ORD record: ord-8ad2f55ea3354d9d9658c58ecd140d4a
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772256B2

Reaction notes

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