HCID 67070084, compound → HCID 67069899, compound

HRID 2390832Notes

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.[Br-].[CH2:21]([Zn+])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:21]([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:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 70 °C

Procedure

step 1—A mixture of 3-(3-bromo-5-tert-butyl-phenyl)-2-methoxy-pyridine (184 mg, 0.575 mmol) and PdCl2(dppf)2 (40 mg, 0.049 mmol) in a Schlenk flask was purged with argon 3 times before THF (5 mL) was added followed by benzylzinc bromide (0.5M in THF, 2.3 mL, 1.150 mmol). The reaction was then heated at 70° C. overnight then cooled to RT, filtered through a pad of CELITE and the filtrate was concentrated. The crude residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (0 to 4% EtOAc) to afford 156 mg (82%) of 3-(3-benzyl-5-tert-butyl-phenyl)-2-methoxy-pyridine (126) as a colorless oil.

Workup

customwas purged with argon 3 times before THF (5 mL)
additionwas added
temperaturethen cooled to RT
filtrationfiltered through a pad of CELITE
concentrationthe filtrate was concentrated
customThe crude residue was purified by SiO2 chromatography
washeluting with an EtOAc/hexane gradient (0 to 4% EtOAc)

Sources & evidence

ORD record: ord-1cd72bfb698c4c63b6e39fad76b3f8b5
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273773B2

Reaction notes

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