Potassium Carbonate → HCID 56849417, compound

HRID 1470339Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=3)[O:10][C:3]=12.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:23]1([C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[C:9]([C:11]4[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=4)[O:10][C:3]=23)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 150 °C

Procedure

7-Chloro-2-(3,4,5-trimethoxy-phenyl)-furo[3,2-b]pyridine (0.061 mmol), phenyl boronic acid (0.064 mmol), palladium(II)-acetate (0.004 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.006 mmol) and K2CO3 (0.181 mmol) are suspended in 1,4-dioxane (1.00 ml) and water (100.00 μl). The suspension is heated to 150° C. in the microwave for 45 min. The solvent is removed in vacuo and the product purified over column chromatography (SiO2, heptan, ethyl acetate). The product is isolated as yellow solid (yield 32%); HPLC (method A): Rt 2.6 min (purity 93.2%); LCMS (ESI+) (method E): Rt 2.416 min, M+H+ 362.1 m/z; 1H NMR (500 MHz, DMSO-d6) δ [ppm] 8.57 (d, J=5.1, 1H), 8.16-8.10 (m, 2H), 7.74 (s, 1H), 7.65 (t, J=7.7, 2H), 7.60 (d, J=5.1, 1H), 7.56 (t, J=7.4, 1H), 7.31 (s, 2H), 3.91 (s, 6H), 3.74 (s, 3H).

Workup

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

Sources & evidence

ORD record: ord-d8e4d6ba49ae4b589eaf9b070e6f04f1
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006440B2

Reaction notes

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