Potassium Carbonate → 7-Chloro-2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridine

HRID 1470338Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9](I)[O:10][C:3]=12.[CH3:12][O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[C:18]([O:22][CH3:23])[C:19]=1[O:20][CH3:21].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:16]3[CH:17]=[C:18]([O:22][CH3:23])[C:19]([O:20][CH3:21])=[C:14]([O:13][CH3:12])[CH:15]=3)[O:10][C:3]=12

Participants

Conditions

Temperature: 150 °C

Procedure

7-Chloro-2-iodo-furo[3,2-b]pyridine (1.467 mmol), 3,4,5-trimethoxybenzene boronic acid (1.539 mmol), palladium(II)-acetate (0.076 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.146 mmol) and K2CO3 (4.399 mmol) are suspended in 1,4-dioxane (11 ml) and water (1.00 ml) is added. The suspension is heated over 45 min at 150° C. in the microwave. The solvent is removed in vacuo. The product is purified over column chromatography (SiO2, heptane, ethyl acetate). The product is isolated as yellow powder (yield 57%); LCMS (method E): 2.43 min (purity 100%), M+H+ 320.0; 1H NMR (500 MHz, DMSO-d6) δ [ppm] 8.45 (d, J=5.3, 1H), 7.79 (s, 1H), 7.49 (d, J=5.2, 1H), 7.29 (s, 2H), 3.91 (s, 6H), 3.75 (s, 3H).

Workup

customThe solvent is removed in vacuo
customThe product is purified over column chromatography (SiO2, heptane, ethyl acetate)

Sources & evidence

ORD record: ord-d9ddeff0b19741f5a2f573e70325a349
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006440B2

Reaction notes

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