Sodium Carbonate → 3-(3-Tert-butyl-4-methoxy-5-nitrophenyl)-2-methoxypyridine

HRID 2390818

Reaction equation

Br[C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[C:5]([O:12][CH3:13])=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:7]=1.[CH3:17][O:18][C:19]1[C:24](B(O)O)=[CH:23][CH:22]=[CH:21][N:20]=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.CO>[C:8]([C:6]1[CH:7]=[C:2]([C:24]2[C:19]([O:18][CH3:17])=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[C:5]=1[O:12][CH3:13])([CH3:11])([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 115 °C

Procedure

step 1—A mixture of 5-bromo-1-tert-butyl-2-methoxy-3-nitrobenzene (0.48 g, 1.7 mmol; CASRN 474554-50-2), 37 (0.28 g, 1.8 mmol), Pd(PPh3)3 (0.19 g, 0.17 mmol) and Na2CO3 (0.53 g, 5.0 mmol) in DCM/MeOH (3:1, 8 mL) was subjected to microwave heating to 115° C. for 35 min. The reaction mixture was filtered and the filtrate concentrated. The crude residue was purified by SiO2 chromatography eluting with EtOAc/hexane to afford 0.44 g (82%) of 3-(3-tert-butyl-4-methoxy-5-nitrophenyl)-2-methoxypyridine (98) as a yellow solid.

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate concentrated
customThe crude residue was purified by SiO2 chromatography
washeluting with EtOAc/hexane

Sources & evidence

ORD record: ord-303d639c3a4c4b1ca35271abfa6ac019
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273773B2

Linked notes

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