Sodium hydride → HCID 59418768, compound

HRID 1896594Notes

Reaction equation

[H-].[Na+].[Br:3][C:4]1[N:9]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[C:7]([OH:14])=[CH:6][CH:5]=1.[O:15]([CH2:22][CH2:23][CH2:24]Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC(N(C)C)=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Br:3][C:4]1[N:9]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[C:7]([O:14][CH2:24][CH2:23][CH2:22][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Sodium hydride (60% in mineral oil, 172 mg, 4.53 mmol) was added to a mixture of methyl 6-bromo-3-hydroxypicolinate (26B) (1.0 g, 4.31 mmol) and 3-phenoxypropyl bromide (927 mg, 4.31 mmol) in DMA (20 mL) at rt. The mixture was heated to 100° C. for 1.75 hours, cooled, diluted with 10% citric acid and extracted with EtOAc. The organic phases were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The crude material was purified by flash column chromatography on silica gel eluting with a gradient of PE:EtOAc 100:0-75:25, to provide 1.35 g (86%) of the desired product methyl 6-bromo-3-(3-phenoxypropoxy)picolinate (26C): 1H NMR (300 MHz, CDCl3) δ 7.52 (1H, d), 7.27 (2H, m), 6.92 (2H, m), 4.25 (2H, t), 4.19 (2H, t), 3.92 (3H, s), 2.30 (2H, t).

Workup

temperaturecooled
extractionextracted with EtOAc
washThe organic phases were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customThe crude material was purified by flash column chromatography on silica gel eluting with a gradient of PE

Sources & evidence

ORD record: ord-30f71fb4d2804fdc84995880fa7b4691
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518970B2

Reaction notes

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