Cesium fluoride → 3-Pyridazin-4-ylbiphenyl-4-ol

HRID 1619624Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].C([Sn](CCCC)(CCCC)[C:20]1[CH:25]=[CH:24][N:23]=[N:22][CH:21]=1)CCC.[F-].[Cs+]>C(#N)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu](I)I>[N:22]1[CH:21]=[CH:20][C:25]([C:2]2[CH:3]=[C:4]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:5]=[CH:6][C:7]=2[OH:8])=[CH:24][N:23]=1

Participants

Conditions

Temperature: 45 °C

Procedure

3-Iodobiphenyl-4-ol (1 g, 3.4 mmol) was mixed with 4-(tributylstannyl)pyridazine (1.25 g 3.4 mmol), caesium fluoride (1.03 g 6.8 mmol), tetrakis(triphenylphosphine) palladium (0) (195 mg, 0.17 mmol) and copper iodide (128 mg 0.68 mmol) in acetonitrile (10 mL). The reaction was degassed 3 times before being placed under nitrogen and heated to 45° C. for 16 hours. The reaction was diluted with acetonitrile (20 mL), washed with heptane (2×20 mL) then absorbed onto silica and purified by silica gel column chromatography (ISCO™, 40 g, 50%-100% ethyl acetate in heptane gradient elution) to afford the title compound (270 mg, 32%) as a pale yellow solid.

Workup

customThe reaction was degassed 3 times
additionThe reaction was diluted with acetonitrile (20 mL)
washwashed with heptane (2×20 mL)
customthen absorbed onto silica
custompurified by silica gel column chromatography (ISCO™, 40 g, 50%-100% ethyl acetate in heptane gradient elution)

Sources & evidence

ORD record: ord-20595fd2e1be40208b9753ad19243e68
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772293B2

Reaction notes

Loading…