Phenol → HCID 67069984, compound

HRID 2390830Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:12]2[C:13]([O:18][CH3:19])=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:5]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:7]=1.[C:20]1([OH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2]>[C:8]([C:6]1[CH:5]=[C:4]([C:12]2[C:13]([O:18][CH3:19])=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:3]=[C:2]([O:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 115 °C

Procedure

step 1—A mixture of 3-(3-bromo-5-tert-butyl-phenyl)-2-methoxy-pyridine (123 mg, 0.384 mmol), phenol (46 mg, 0.489 mmol), Pd(OAc)2 (4.1 mg, 0.018 mmol), 2-di-tert-butylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (9.9 mg, 0.023 mmol) and K3PO4 (167 mg, 0.787 mmol)) in a Schlenk flask was purged with argon before toluene (5 mL) was added. The reaction under an argon atmosphere was heated overnight at 115° C. The reaction was cooled to RT, filtered through CELITE, and the filtrate was concentrated. The crude residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (0 to 2% EtOAc) to afford 40 mg (41%) of 3-(3-tert-butyl-5-phenoxy-phenyl)-2-methoxy-pyridine (124).

Workup

customwas purged with argon before toluene (5 mL)
additionwas added
customThe reaction under an argon atmosphere
temperatureThe reaction was cooled to RT
filtrationfiltered through CELITE
concentrationthe filtrate was concentrated
customThe crude residue was purified by SiO2 chromatography
washeluting with an EtOAc/hexane gradient (0 to 2% EtOAc)

Sources & evidence

ORD record: ord-78f06c60dfe74f93a7e636252df4e286
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273773B2

Reaction notes

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