Potassium Carbonate → HCID 66779938, compound

HRID 1470355Notes

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.[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.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]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=3)[O:10][C:3]=12

Participants

Conditions

Temperature: 150 °C

Procedure

To a 30 mL microwave vial with stirbar was added 7-chloro-2-iodo-furo[3,2-b]pyridine (300.00 mg; 1.07 mmol; 1.00 eq.), 4-fluorophenylboronic acid (157.71 mg; 1.13 mmol; 1.05 eq.), palladium(II) acetate (12.05 mg; 0.05 mmol; 0.05 eq.), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (44.07 mg; 0.11 mmol; 0.10 eq.), and potassium carbonate (445.09 mg; 3.22 mmol; 3.00 eq.). Reagents were suspended in dioxane (6.00 ml)/water (0.60 ml) under N2 and heated in microwave reactor at 150° C. for 15 min. The reaction mixture was cooled to room temperature and concentrated on a rotary evaporator. The crude mixture was purified by Biotage chromatography (20-100% EtOAc/hex 30 column vol.) to afford the title compound as a white solid (152 mg, 57%). (HPLC (method F): 95%, RT: 7.11 min); 1H NMR (400 MHz, DMSO-d6) δ [ppm] 8.47 (d, J=5.2, 1H), 8.11-8.05 (m, 2H), 7.79 (s, 1H), 7.53 (d, J=5.3, 1H), 7.47-7.39 (m, 2H); MS (m/z) 248 [M+H]+, RT: 3.9 min.

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated on a rotary evaporator
customThe crude mixture was purified by Biotage chromatography (20-100% EtOAc/hex 30 column vol.)

Sources & evidence

ORD record: ord-1bc35ea28d854020929c16b2876d444f
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006440B2

Reaction notes

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